cas 22415-91-4, ALPHA-D-GLUCOPYRANOSE PENTABENZOATE

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Towards the development of a targeted albumin-binding radioligand: Synthesis, radiolabelling and preliminary in vivo studies
Introduction: The compound named 4-[10-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanamido)decyl]-11-[10-(β,D-glucopyranos-1-yl)-1-oxodecyl]-1,4,8,11-tetraazacyclotetradecane-1,8-diacetic acid is a newly synthesised molecule capable of binding in vivo to
Driver, Cathryn Helena Stanford,Ebenhan, Thomas,Szucs, Zoltan,Parker, Mohammed Iqbal,Zeevaart, Jan Rijn,Hunter, Roger
p. 53 - 66
(2021/02/09)

Synthesis and inhibition of α-glucosidase of methyl glycyrrhetinate glycosides
The synthesis of the methyl glycyrrhetinate glycosides and inhibition of α-glucosidase were studied. The carboxyl group of glycyrrhetinic acid was methylated, and glucose and galactose were introduced into the hydroxyl group to obtain compounds 7 and 12.
Zhang, Wei,Wang, He-Ying,Wang, Huai-Xu,Zhu, Zhen-Yuan
supporting information
p. 1874 - 1880
(2019/07/22)

Synthesis, molecular docking analysis and biological evaluations of saccharide-modified thiadiazole sulfonamide derivatives
A series of saccharide-modified thiadiazole sulfonamide derivatives has been designed and synthesized by the “tail approach” and evaluated for inhibitory activity against carbonic anhydrases II, IX, and XII. Most of the compounds showed high topological polar surface area (TPSA) values and excellent enzyme inhibitory activity. The impacts of some compounds on the viability of HT-29, MDA-MB-231, and MG-63 human cancer cell lines were examined under both normoxic and hypoxic conditions, and they showed certain inhibitory effects on cell viability. Moreover, it was found that the series of compounds had the ability to raise the pH of the tumor cell microenvironment. All the results proved that saccharide-modified thiadiazole sulfonamides have important research prospects for the development of CA IX inhibitors.
Zhang, Zuo-Peng,Zhong, Ye,Han, Zhen-Bin,Zhou, Lin,Su, Hua-Sheng,Wang, Jian,Liu, Yang,Cheng, Mao-Sheng
(2021/05/26)

A Substituent-Directed Strategy for the Selective Synthesis of L-Hexoses: An Expeditious Route to L-Idose
L-Hexoses are rare but biologically significant components of various important biomolecules. However, most are prohibitively expensive (if commercially available) which limits their study and biotechnological exploitation. New, efficient methods to access L-hexoses and their derivatives are thus of great interest. In a previous study, we showcased a stereoselective Bu3SnH-mediated transformation of a 5-C-bromo-D-glucuronide to an L-iduronide. We have now drawn inspiration from this result to derive a new methodology – one that can be harnessed to access other L-hexoses. DFT calculations demonstrate that a combination of a β-F at the anomeric position and a methoxycarbonyl substituent at C-6 is key to optimising the selectivity for the L-hexose product. Our investigations have also culminated in the development of the shortest known synthetic route to a derivative of L-idose from a commercially available starting material (45 % yield over 3 steps). Collectively, these results address the profound lack of understanding of how to synthesise L-hexoses in a stereoselective fashion.
See, Nicholas W.,Wimmer, Norbert,Krenske, Elizabeth H.,Ferro, Vito
p. 1575 - 1584
(2021/03/03)

N-aryl sulfanilamide-N-beta-D-glucopyranose diamide compound and application thereof
The invention belongs to the technical field of medicines, and relates to a preparation method and medical application of an N1-aryl sulfanilamide-N4-beta-D-glucopyranose diamide compound. The compound is shown in a general formula (I), substituent groups are described in the specification, and the compound shown in the general formula (I) and an optical active body, a diastereoisomer and a pharmaceutically acceptable salt thereof are applied to preparation of anti-tumor drugs. Based on pharmacophore characteristics and subcellular localization of CA IX and XII, a selective CA IX and XII inhibitor is designed and synthesized, polyhydroxy high-polarity glucose is selected as a tail end, a classical pharmacophore aryl sulfanilamide fragment of a targeted CAs active center is introduced through a flexible aliphatic chain and a rigid aromatic structure, the overall structure can selectively inhibit catalytic activity of extracellular CA IX and XII, an anti-tumor effect is achieved, and therefore, the compound has a good application prospect.
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Paragraph 0029-0030

(2021/06/26)

Preparation method of glycyrrhetinic acid glucoside and application of glycyrrhetinic acid glucoside in sweetening agents
The invention relates to a synthetic route of glycyrrhetinic acid glucoside and application of glycyrrhetinic acid glucoside in sweetening agents, and belongs to the field of synthesis of novel sweetening agents. The novel sweetening agent with higher swe
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Paragraph 0007; 0015; 0018

(2020/07/29)

PROCESS FOR PREPARING MANNOSE DERIVATIVES
The invention relates to a process to prepare a compound of the following formula (I): (I), in which P represents a protective group of a hydroxyl function which is a -COR1 group with R1 representing an aryl or a (C1C
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Page/Page column 27

(2020/02/16)

Melophluosides A and B, new triterpene galactosides from the marine sponge Melophlus sarasinorum
Two new triterpene galactosides, melophluosides A and B, were isolated from a marine sponge Melophlus sarasinorum collected in Indonesia. Their structures were determined by the analysis of spectroscopic data and chemical reactions. The absolute configuration of cyclohexenone moiety was determined by the calculated ECD spectrum of a simplified model. Melophluosides A and B exhibited moderate cytotoxicity against HeLa cells (IC50, 11.6 and 9.7 μM, respectively).
Angkouw, Esther D.,Fukumoto, Arina,Hitora, Yuki,Ise, Yuji,Mangindaan, Remy E. P.,Sadahiro, Yusaku,Tsukamoto, Sachiko
(2020/04/08)

Synthesis of 2-deoxy-d-glucose coated Fe3O4nanoparticles for application in targeted delivery of the Pt(iv) prodrug of cisplatin-a novel approach in chemotherapy
A water soluble Pt(iv) prodrug of cisplatin was synthesized by oxidation of cisplatin followed by treatment with succinic anhydride to achieve easily reducible ester linkage at axial positions which was evidenced from cyclic voltammetric analyses. Because of this modification the Pt(iv) prodrug achieved better physicochemical and pharmacological properties like water solubility and reduced toxicity for normal (non-cancerous) CHO cells respectively, as compared to cisplatin. Later, this Pt(iv) prodrug was loaded on 2-deoxy-d-glucose (2DG) functionalized over silica coated Fe3O4 magnetic nanoparticles (MNPs) to achieve the desired formulation. It exhibited potency as evidenced from the cytotoxicity evaluation against MCF-7 human breast cancer cell lines (IC50 ～ 14 μM). This encouraged us to further study the percentage viability, apoptosis and cell death evaluations on MCF-7, Colo-205 and CHO cells by flow cytometry. The cytotoxic potency of the formulation towards cancer cells, Colo-205 and MCF-7 (22-30% apoptosis), was revealed while the parent formulation was non-toxic to non-cancerous, CHO cell lines (3% apoptosis) as compared to cisplatin. It revealed that the formulation is comparable to cisplatin in its cell killing efficiency. Additionally the FITC labeled MNPs coated with 2DG exhibited efficient cell uptake and fast internalization (within 3 h) accumulating mainly in the cytoplasm and at the cell surface. Besides this, the formulation exhibited heating efficacy suggesting its possible application for hyperthermia treatment also. These results indicate the possible utility of the formulation for site specific delivery of the Pt(iv) prodrug of cisplatin. This journal is
Ballal, Anand,Dubey, Akhil K.,Koijam, Arunkumar S.,Kumar, Chandan,Mukherjee, Sudip,Phadnis, Prasad P.,Sharma, K. Shitaljit,Vatsa, Rajesh K.
supporting information
p. 13863 - 13874
(2020/09/07)

A Synthetic Carbohydrate-Protein Conjugate Vaccine Candidate against Klebsiella pneumoniae Serotype K2
Klebsiella pneumoniae causes pneumonia and liver abscesses in humans worldwide and contains virulence factor capsular polysaccharides and lipopolysaccharides linked to the cell wall. Although capsular polysaccharides are good antigens for vaccine producti
Ravinder, Mettu,Liao, Kuo-Shiang,Cheng, Yang-Yu,Pawar, Sujeet,Lin, Tzu-Lung,Wang, Jin-Town,Wu, Chung-Yi
p. 15964 - 15997
(2020/11/13)

Delta-oleanolic acid saponin compound and medical application thereof
The invention discloses a delta-oleanolic acid saponin compound and medical application thereof. The delta-oleanolic acid saponin compound is a compound with a structural formula shown as a formula (I), and pharmaceutically acceptable salt or ester or pro
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Paragraph 0074-0077

(2020/12/31)

The synthesis of rare earth metal-doped upconversion nanoparticles coated with d-glucose or 2-deoxy-d-glucose and their evaluation for diagnosis and therapy in cancer
Rare earth metal-doped upconversion nanoparticles (UCNPs) are emerging as a new class of biomedical imaging materials due to their higher energy anti-Stokes shift, high optical penetration depth and long term repetitive imaging. In the present study, upconversion nanoparticles based on NaYF4 doped with thulium (Tm) and ytterbium (Yb) were prepared via a thermolysis method using oleic acid as a capping agent and 1-octadecene as a solvent. The X-ray diffraction pattern of the synthesized nanoparticles was found to match the standard hexagonal phase. The nanoparticles were coated with silica using tetraethyl orthosilicate (TEOS) and in order to avoid agglomeration, IGEPAL CO-520 was used as the surfactant. The coatings of SiO2 over NaYF4 were confirmed by the TEM image and XRD pattern. NaYF4@SiO2 was further functionalized by the addition of (3-aminopropyl)trimethoxysilane (APTMS) followed by either d-glucose or 2-deoxy-d-glucose (2-DG). UCNPs-d-glucose and UNCPs-2DG were examined for cell viability (MCF-7 cells) by MTT assay. The cellular uptake of UCNPs in MCF-7 cells was seen in terms of emission of a blue light. Furthermore, the uptake rate of UCNPs coated with 2-deoxy-d-glucose was found to be much faster than that of UCNPs alone under d-glucose starved conditions. The functionalization of UCNPs with 2-deoxy-d-glucose (2-DG) not only increased the uptake of nanoparticles, but also blocked the glycolysis pathway resulting in the inhibition of tumor growth as 2-deoxy-d-glucose (2-DG) is mimicking the d-glucose. The results are indicative that these upconversion nanoparticles may find applications in bio-imaging, removal of tumor by precision surgery, therapy and targeted drug delivery. This journal is
Sharma, K. Shitaljit,Thoh, Maikho,Dubey, Akhil K.,Phadnis, Prasad P.,Sharma, Deepak,Sandur, Santosh K.,Vatsa, Rajesh K.
supporting information
p. 13834 - 13842
(2020/09/07)

Aralia saponin derivative as well as preparation method and application thereof (by machine translation)
The invention discloses an Aralia saponin derivative as well as a preparation method and application, thereof. A structure represented by the general formula (I). To the invention, oleanolic acid and four sugar, coffee acid or 3 - methoxy 4 - hydroxycinna
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Paragraph 0095-0100

(2019/08/20)

Aralia elata seem monomer saponin derivative and preparation method and use thereof
The invention discloses an aralia elata seem monomer saponin derivative and a preparation method and use thereof. The derivative has a structure represented by a general formula (I). Oleanolic acid orursolic acid, five kinds of sugars and caffeic acid are
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Paragraph 0107-0112

(2019/08/30)

Impact of Aromatic Stacking on Glycoside Reactivity: Balancing CH/πand Cation/πInteractions for the Stabilization of Glycosyl-Oxocarbenium Ions
Carbohydrate/aromatic stacking represents a recurring key motif for the molecular recognition of glycosides, either by protein binding domains, enzymes, or synthetic receptors. Interestingly, it has been proposed that aromatic residues might also assist i
Montalvillo-Jiménez, Laura,Santana, Andrés G.,Corzana, Francisco,Jiménez-Osés, Gonzalo,Jiménez-Barbero, Jesús,Gómez, Ana M.,Asensio, Juan Luis
supporting information
p. 13372 - 13384
(2019/09/10)

Synthesis of 12- O-Mono- and Diglycosyl-oxystearates, a New Class of Agonists for the C-type Lectin Receptor Mincle
Fifteen glycosyl-oxystearates were synthesized by Crich's 4,6-benzylidene and K?ening-Knorr strategies. Assessment of structure-activity relationships using macrophage-inducible C-type lectin (Mincle) receptor cells expressing nuclear factor of activated
Van Huy, Le,Tanaka, Chiaki,Imai, Takashi,Yamasaki, Sho,Miyamoto, Tomofumi
supporting information
p. 44 - 49
(2019/01/15)

Convenient synthesis of the immunogenic glycolipid BbGL1
A simple and efficient method to synthesize the immunogenic glycolipid BbGL1 is introduced. Two simple steps were required to obtain the desired product in good yield. First, a highly efficient glycosylation of cholesterol using galactosyl trichloroacetim
J?ger, Sebastián N.,Porta, Exequiel O.J.,Labadie, Guillermo R.
p. 41 - 45
(2018/11/30)

Ionic liquid-assisted catalysis for glycosidation of two triterpenoid sapogenins
In order to both investigate the universality of ionic liquid-based catalytic systems for synthesis of triterpene saponins and explore their effective application methods together with the catalytic behaviors of ionic liquids in related reactions by comparison between different initiators, oleanolic acid and ursolic acid were selected to establish a catalytic system for glycosylation in this study as typical representatives of pentacyclic triterpene sapogenins. As a result, it was found that the system of [C4mim][OTf] + TMSOTf in the reactions between the glycosyl receptors and donors showed obvious catalytic effects; also, the system was stable and could be recycled. The functions of IL include solvent, cocatalyst and stabilizer, simultaneously; thus, the current catalytic system is greener, simpler and more efficient. The reaction time was short, and only β-type products were obtained. This study offers a reference for developing a new glucoside synthesis technology and provides sufficient preliminary exploration and basic data for further large-scale applications.
Zhang, Tenghe,Li, Xinlu,Song, Hang,Yao, Shun
p. 16881 - 16888
(2019/11/14)

Lewis acid promoted anomerisation of alkyl O- and S-xylo-, arabino- and fucopyranosides
Pentopyranoside and 6-deoxyhexopyranosides, such as those from D-xylose, L-arabinose and L-fucose are components of natural products, oligosaccharides or polysaccharides. Lewis acid promoted anomerisation of some of their alkyl O- and S-glycopyranosides i
Doyle, Lisa M.,Meany, Fiach B.,Murphy, Paul V.
supporting information
p. 85 - 94
(2018/12/05)

Synthesis of Thioglycosides with Nitrogen-Containing Heterocyclic Fragments
A number of thioglycosides derived from benzoylated glucopyranose and nitrogen-containing heterocyclic thiols have been synthesized in up to 98% yield, and benzoyl protecting groups have been removed from the glycoside with a 3-phenyl-4-oxo-3,4-dihydroqui
Pestova,Izmest’ev,Rubtsova,Polukeev,Kutchin
p. 1041 - 1044
(2018/09/11)

ENDOSOMAL CLEAVABLE LINKERS
The present disclosure relates generally to cleavable linkers and uses thereof.
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Paragraph 00563

(2018/08/20)

Deciphering the conformation of C-linked α-D-mannopyranosides and their application toward the synthesis of low nanomolar E. Coli FimH ligands
C-Allyl –D-mannopyranosides were prepared via a variety of routes to determine an optimal route to the - anomers. The relative conformational energies of the key intermediate was evaluated by molecular modeling which showed the conventional4Cs
Mousavifar, Leila,Vergoten, Gérard,Roy, René
p. 384 - 397
(2019/01/03)

Stereoselective Epimerizations of Glycosyl Thiols
Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective β-d-manno- and β-l-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation.
Doyle, Lisa M.,O'Sullivan, Shane,Di Salvo, Claudia,McKinney, Michelle,McArdle, Patrick,Murphy, Paul V.
supporting information
p. 5802 - 5805
(2017/11/10)

The dehydroepiandrosterone and dehydroepiandrosterone alkone glycosylation derivative and its preparation method and application
The invention discloses epiandrosterone glycosylation derivatives and dehydrogenated epiandrosterone glycosylation derivatives, and a preparation method thereof. The preparation method comprises the following steps: respectively carrying out coupling reac
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Paragraph 0041; 0042

(2017/04/28)

3 - monosaccharide acid oxygen glucoside oleanolic alkane type and wusu alkane triterpene saponin derivative and its preparation method and application
The invention discloses a 3-monouronic acid o-glycoside oleanane type and ursane type triterpenoid saponin derivative. The derivative has a structural formula as shown in the specification, wherein R4 is one of H atom, alkyl containing 1-10 carbons, alkyl
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Paragraph 0035; 0036

(2017/08/25)

Sites for dynamic protein-carbohydrate interactions of O- and C-linked mannosides on the E. coli FimH adhesin
Antagonists of the Escherichia coli type-1 fimbrial adhesin FimH are recognized as attractive alternatives for antibiotic therapies and prophylaxes against acute and recurrent bacterial infections. In this study α-D-mannopyranosides O- or C-linked with an
Touaibia, Mohamed,Krammer, Eva-Maria,Shiao, Tze C.,Yamakawa, Nao,Wang, Qingan,Glinschert, Anja,Papadopoulos, Alex,Mousavifar, Leila,Maes, Emmanuel,Oscarson, Stefan,Vergoten, Gerard,Lensink, Marc F.,Roy, René,Bouckaert, Julie
supporting information

(2017/08/30)

Metal-free and VOC-free: O -glycosylation in supercritical CO2
Supercritical carbon dioxide (scCO2) is a suitable medium to perform transition metal-free glycosylation reactions in the absence of volatile organic solvents (VOCs) using glycosyl halides as glycosyl donors. The methodology described here can be applied for obtaining O-glycosides in a totally green reaction, as well as orthoesters, depending on the reaction conditions. The process is much more sensitive to temperature changes than to pressure modification, with glycosyl chlorides requiring higher temperatures to be activated than glycosyl bromides. Pivaloyl groups act as good CO2-philic units and are shown to be the best choice to obtain good stereoselectivities. The relevance of the fluid nature and supercritical conditions was also evidenced.
Cardona, Adrià,Boutureira, Omar,Castillón, Sergio,Díaz, Yolanda,Matheu, M. Isabel
supporting information
p. 2687 - 2694
(2017/07/17)

Isoquinoline-1-Carboxylate as a Traceless Leaving Group for Chelation-Assisted Glycosylation under Mild and Neutral Reaction Conditions
Glycosyl isoquinoline-1-carboxylate was developed as a novel benchtop stable and readily available glycosyl donor. The glycosylation reaction was promoted by the inexpensive Cu(OTf)2 salt under mild reaction conditions. The copper isoquinoline-1-carboxylate salt was precipitated from the solution and thus rendered a traceless leaving group. Surprisingly, the proton from the acceptor was absorbed by the precipitated metal complex and the reaction mixture remained at neutral pH. The copper-promoted glycosylation was also proven to be completely orthogonal to the gold-promoted glycosylation, and an iterative synthesis of oligosaccharides from benchtop stable anomeric ester building blocks becomes possible under mild reaction conditions.
Wang, Hao-Yuan,Simmons, Christopher J.,Blaszczyk, Stephanie A.,Balzer, Paul G.,Luo, Renshi,Duan, Xiyan,Tang, Weiping
supporting information
p. 15698 - 15702
(2017/11/13)

Practical synthesis of latent disarmed S-2-(2-propylthio)benzyl glycosides for interrupted Pummerer reaction mediated glycosylation
Practical synthetic methods to latent disarmed S-2-(2-propylthio)benzyl (SPTB) glycosides for interrupted Pummerer reaction mediated glycosylation have been discovered. Among them, both coupling reaction of PTB-Cl with glycosyl thiols and BF3·OEt2 promoted reaction of peracylated glycosides with PTB-SH produced peracylated SPTB glycosides in large scales and with high efficiency.
Xu, Yang,Zhang, Qian,Xiao, Ying,Wu, Pinru,Chen, Wei,Song, Zejin,Xiao, Xiong,Meng, Lingkui,Zeng, Jing,Wan, Qian
supporting information
p. 2381 - 2384
(2017/05/29)

RADIOPHARMACEUTICAL CONJUGATE
This invention relates new radiopharmaceutical conjugates for use in improved methods of diagnosis and treatment of cancer. The radiopharmaceutical conjugate comprises, in sequence: a metabolite that targets tumour cells, bound to a chelating agent capable of containing a radionuclide.bound to a linker capable of binding with an EPR agent in vitro or in vivo; or a chelating agent capable of containing a radionuclide, bound to a metabolite that targets tumour cells, bound to a linker capable of binding with an EPR agent in vitro or in vivo. The radiopharmaceutical conjugates of the present invention provide active and passive targeted radionuclide delivery systems that can help to improve the biodistribution and pharmacological toxicity of the radiopharmaceuticals used for the diagnosis and therapy of cancer.
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Page/Page column 33

(2016/04/20)

Preparation and activity evaluation of chrysin-β-d-galactopyranoside
Chrysin-β-d-galactopyranoside was efficiently synthesized, evaluated for its inhibitory activities against H22 cell lines compared with chrysin, the scavenging of hydroxyl radical, DPPH radical and superoxide anion, inhibitory effect against bacteria and
Zhu, Zhen-Yuan,Chen, Ling,Liu, Fei,Chen, Li-Jing,Meng, Meng,Sun, Hui-Qing,Zhang, Yong-Min
p. 1433 - 1440
(2016/10/20)

Flavone glycoside derivatives, and preparation method and application thereof
The invention discloses flavone glycoside derivatives which are compounds with a general structural formula I shown in the description, and pharmaceutically acceptable salts or hydrates thereof, including racemates, optical isomers and epimers of the deri
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Paragraph 0060; 0061; 0062

(2016/10/08)

2′-Deoxy-2′,2′-difluorothymidine analogues for radiolabeling with fluorine-18 and other biomedical applications
Novel 2′-deoxy-2′,2′-difluorothymidine analogues with potential applications as antiviral, cytotoxic and cancer imaging agents have been synthesized. Introduction of the hydroxymethyl functionality at the 5-position of 2′-deoxy-2′,2′-difluoruridine provided a key intermediate with a suitable synthetic handle for the generation of these nucleoside derivatives.
Doepner, Andreas M.,Aboagye, Eric O.,Barrett, Anthony G.M.
supporting information
p. 3293 - 3297
(2015/03/04)

Synthesis of a 1,3 β-glucan hexasaccharide designed to target vaccines to the dendritic cell receptor, Dectin-1
Transformation of 3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-d-glucofuranose into 2,4,6-tri-O-benzoyl-3-O-benzyl glucopyranosyl imidate proceeded efficiently via crystalline benzyl and per-benzoylated derivatives. This imidate glycosylated di-O-isopropylidene-α-d-glucofuranose in high yield and glycosylation of the disaccharide after removal of the 3′-O-benzyl ether afforded the β1,3 linked trisaccharide in excellent yield. Di- and trisaccharides imidates were readily prepared from the furanose terminated glycosylation products but both were unreactive in glycosylation reaction with the debenzylated di- and trisaccharide alcohols. The 3′-O-benzyl perbenzoylated disaccharide pyranose derivative could be selectively debenzoylated and converted to the corresponding perbenzoylated 4,6:4′,6′-di-O-benzylidene derivative. Lewis acid catalyzed glycosidation gave the selectively protected disaccharide ethylthioglycoside in good overall yield. Glycosidation of this thioglycoside donor with 5-methoxycarbonylpentanol gave the disaccharide tether glycoside and after catalytic removal of benzyl ether the resulting disaccharide alcohol was glycosylated by the thioglycoside in a 2+2 reaction to yield a tetrasaccharide. Repetition of selective deprotection of the terminal 3-O-benzyl ether followed by glycosylation by the disaccharide thioglycoside gave a protected hexasaccharide. Hydrogenolysis of this hexasaccharide followed by transesterification and second hydrogenolysis to remove a residual benzyl group gave the target hexasaccharide glycoside 1 as a Dectin-1 ligand functionalized to permit covalent attachment to glycoconjugate vaccines and thereby facilitate improved antigen processing by dendritic cells.
Elsaidi, Hassan R.H.,Paszkiewicz, Eugenia,Bundle, David R.
p. 96 - 106
(2015/04/14)

3-(Dimethylamino)-1-propylamine: A cheap and versatile reagent for removal of byproducts in carbohydrate chemistry
Inexpensive 3-(dimethylamino)-1-propylamine (DMAPA) was found to be effective in anomeric deacylation reactions giving 1-O deprotected sugars in high yield as precursors for the formation of imidate glycosyl donors. DMAPA was also found to be useful for removing excess reagents such as benzoyl chloride, tosyl chloride, and 2,2,2-trifluoro-N-phenylacetimidoyl chloride. The deacylation reaction could be conducted in moist THF and did not require chromatographic purification since an acidic wash was sufficient to remove excess reagent and the formed byproduct.
Andersen, Sofie Meng,Heuckendorff, Mads,Jensen, Henrik H.
supporting information
p. 944 - 947
(2015/04/14)

Regiospecific anomerisation of acylated glycosyl azides and benzoylated disaccharides by using TiCl4
Chelation induced anomerisation is promoted when Lewis acids, such as TiCl4 or SnCl4, coordinate to the pyranose ring oxygen atom and another site, giving rise to endocyclic cleavage and isomerisation to the more stable anomer. In this research regiospecific site-directed anomerisation is demonstrated. TiCl4 (2.5equiv) was employed to induce anomerisation of 15 glycosyl azide and disaccharide substrates of low reactivity, and high yields (>75 %) and stereoselectivies (α/β>9:1) were achieved. The examples included glucopyranuronate, galactopyranuronate and mannopyranuronate as well as N-acetylated glucopyranuronate and galactopyranuronate derivatives. A disaccharide with the α1→4 linkage found in polygalacturonan was included. The use of benzoylated saccharides was found to be important in disaccharide anomerisation as attempts to isomerise related acetyl protected and 2,3-carbonate protected derivatives were not successful. Copyright
Farrell, Mark,Zhou, Jian,Murphy, Paul V.
supporting information
p. 14836 - 14851
(2013/11/06)

A facile synthesis of N/C-terminal selenourea tethered glycosylated amino acids
A simple route for the synthesis of a new class of neoglycosylated amino acids possessing a selenourea moiety is described. The coupling of a-isoselenocyanato esters or Cbz/Boc-amino alkyl isoselenocyanates with peracetyl/benzoylated glucosylamine at ambient temperature led to insert selenourea as a linker. All the compounds prepared have been isolated as analytically pure ones, and characterized by 1H. 13C and 77Se NMR, and mass spectroscopy.
Sureshbabu, Vommina V.,Vasantha,Madhu
p. 895 - 900
(2013/08/15)

Efficient synthesis of building blocks for branched rhamnogalacturonan i fragments
Starting from allyl 2-O-acetyl-3-O-benzyl-α-l-rhamnopyranoside (3), allyl (2,3,4,6-tetra-O-benzoyl-β-d-galactopyranosyl)-(1→4)-2-O-acetyl- 3-O-benzyl-α-l-rhamnopyranoside (5) was synthesized under Helferich conditions. Module 5 was converted to 2,3,4,6-te
Pogosyan, Amayak,Gottwald, Andreas,Michalik, Dirk,Endress, Hans-Ulrich,Vogel, Christian
p. 9 - 15
(2013/10/01)

TIMOSAPONIN COMPOUNDS
Provided herein are timosaponin compounds of Frmula I, II, IIΙ, I', II' and IIΙ', pharmaceutical compositions comprising the coumpounds, and processes of preparation thereof. Also provided are uses of said timosaponin compounds for preparing medicament for the treatment of diseases associated with beta-amyloid in hosts or subjects in need thereof.
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Paragraph 00244

(2013/10/22)

Synthesis and evaluation of four hederagenin glycosides as α-glucosidase inhibitor
The four hederagenin glycosides 1-4 were efficiently synthesized through one-pot sequential glycosylations with glycose 1-(trichloroacetimidate)s as donors, resulting in a significantly simplified synthetic procedure without isolation of glycosylation intermediates. The activity of the synthetic hederagenin glycosides 1-4 against α-glucosidase type IV was evaluated; hederagenin glycoside 4 containing an α-L-rhamnopyranosyl unit showed the best activity with an IC50 value of 47.9 μM. Copyright
Liu, Qing-Chao,Guo, Tian-Tian,Guo, Shou-Dong,Li, Wen-Hong,Li, Dong
p. 142 - 149
(2013/03/14)

A novel "pro-sensitizer" based sensing of enzymes using Tb(iii) luminescence in a hydrogel matrix
Chemically synthesized "pro-sensitizers" release the sensitizer in the presence of lipase or β-glucosidase, triggering a significant luminescence response from a lanthanide based hydrogel. The Royal Society of Chemistry 2012.
Bhowmik, Sandip,Maitra, Uday
supporting information; experimental part
p. 4624 - 4626
(2012/06/05)

Cross metathesis assisted solid-phase synthesis of glycopeptoids
A solid-phase synthesis of glycopeptoids was explored through olefin cross metathesis (CM). Peptoids and sugar derivatives with appropriate olefin moieties were coupled in the presence of an olefin metathesis catalyst to afford glycopeptoids in good yield
Khan, Sharaf Nawaz,Kim, Arim,Grubbs, Robert H.,Kwon, Yong-Uk
supporting information; scheme or table
p. 2952 - 2955
(2012/07/30)

Highly efficient synthesis and antitumor activity of monosaccharide saponins mimicking components of Chinese folk medicine Cordyceps sinensis
Ergosterol 3-O-β-d-glucopyranoside (1a) and ergosterol 3-O-d-galactopyranoside (1b) were highly efficiently synthesized and evaluated for their inhibitory activities against two tumor cell lines. The structures of these compounds were extensively confirmed by 1H, 13C NMR, IR, and HRMS. Compounds 1a and 1b exhibited interesting cytotoxic profiles. The antitumor activity of compound 1a was higher than that of 1b.
Zhu, Zhen-Yuan,Yao, Qiang,Liu, Yang,Si, Chuan-Ling,Chen, Jing,Liu, Nian,Lian, Hong-Yu,Ding, Li-Na,Zhang, Yong-Min
scheme or table
p. 429 - 435
(2012/10/07)

Benzoylated ethyl 1-thioglycosides: Direct preparation from per-O-benzoylated sugars
d-Glucose, lactose, maltose, and melibiose were benzoylated with Bz 2O-Et3N reagent to give fully benzoylated β products. Under the same conditions, d-mannose produced a mixture where the β-benzoate predominated. Treatment of the foregoing compounds with EtSH at slightly elevated temperature (50-60 °C) in the presence of BF 3·Et2O as a promoter gave the corresponding ethyl 1-thio glycosides in high yields. The α-products predominated in all cases in the anomeric mixtures formed. Individual products of all reactions were isolated by chromatography, they were obtained in analytically pure state, and were fully characterized by 1H and 13C NMR data and physical constants.
Sail, Deepak,Kovac, Pavol
scheme or table
p. 47 - 52
(2012/09/22)

Saccharide-modified nanodiamond conjugates for the efficient detection and removal of pathogenic bacteria
The detection and removal of bacteria, such as E. coli in aqueous environments by using safe and readily available means is of high importance. Here we report on the synthesis of nanodiamonds (ND) covalently modified with specific carbohydrates (glyco-ND) for the precipitation of type 1 fimbriated uropathogenic E. coli in solution by mechanically stable agglutination. The surface of the diamond nanoparticles was modified by using a Diels-Alder reaction followed by the covalent grafting of the respective glycosides. The resulting glyco-ND samples are fully dispersible in aqueous media and show a surface loading of typically 0.1 mmol g-1. To probe the adhesive properties of various ND samples we have developed a new sandwich assay employing layers of two bacterial strains in an array format. Agglutination experiments in solution were used to distinguish unspecific interactions of glyco-ND with bacteria from specific ones. Two types of precipitates in solution were observed and characterized in detail by light and electron microscopy. Only by specific interactions mechanically stable agglutinates were formed. Bacteria could be removed from water by filtration of these stable agglutinates through 10 μm pore-size filters and the ND conjugate could eventually be recovered by addition of the appropriate carbohydrate. The application of glycosylated ND allows versatile and facile detection of bacteria and their efficient removal by using an environmentally and biomedically benign material. Copyright
Hartmann, Mirja,Betz, Patrick,Sun, Yuchen,Gorb, Stanislav N.,Lindhorst, Thisbe K.,Krueger, Anke
supporting information; experimental part
p. 6485 - 6492
(2012/06/16)

Mitochondrial affinity of guanidine-rich molecular transporters built on monosaccharide scaffolds: Stereochemistry and lipophilicity
We synthesized eight G8 molecular transporters (MTs) based on 4 different monosaccharide scaffolds, and studied their biological properties with a special focus on possible mitochondrial targeting and tissue selectivity. The mitochondrial affinity of these MTs was found to be clearly related to the scaffold stereochemistry and also tenuously with the lipophilicity. It may be suggested that in the practical delivery strategy of drugs for the brain and mitochondrial diseases the BBB permeability and mitochondrial affinity should be considered as key parameters, and that an enhanced mitochondrial affinity appears possible by further research on the structure-property relationship of guanidine-rich molecular transporters.
Lee, Woo Sirl,Kim, Wanil,Kim, Kyong-Tai,Chung, Sung-Kee
experimental part
p. 2286 - 2300
(2012/06/16)

DABCO: An efficient promoter for the acetylation of carbohydrates and other substances under solvent-free conditions
A simple, mild and efficient solvent-free method for the acetylation of carbohydrates, and their partially protected derivatives, as well as non-carbohydrate substances in excellent yields in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) is described with the advantage of tolerance to various functional groups, short reaction time and ease of product isolation.
Ch, Ratnasekhar,Tyagi, Mohit,Patil, Premanand Ramrao,Kartha, K.P. Ravindranathan
scheme or table
p. 5841 - 5846
(2011/12/03)

Synthesis of some phenylpropanoid glycosides (PPGs) and their acetylcholinesterase/xanthine oxidase inhibitory activities
In this research, three categories of phenylpropanoid glycosides (PPGs) were designed and synthesized with PPGs isolated from Rhodiola rosea L. as lead compounds. Their inhibitory abilities toward acetylcholinesterase (AChE) and xanthine oxidase (XOD) were also tested. Some of the synthetic PPGs exhibited excellent enzyme inhibitory abilities.
Li, Xiao-Dong,Kang, Shuai-Tao,Li, Guo-Yu,Li, Xian,Wang, Jin-Hui
experimental part
p. 3580 - 3596
(2011/07/07)

Antifungal activity of 2α,3β-functionalized steroids stereoselectively increases with the addition of oligosaccharides
Invasive fungal infections pose a significant problem to the immune-compromised. Moreover, increased resistance to common antifungals requires development of novel compounds that can be used to treat invasive fungal infections. Naturally occurring steroid
Cammarata, Amy,Upadhyay, Sunil Kumar,Jursic, Branko S.,Neumann, Donna M.
supporting information; experimental part
p. 7379 - 7386
(2012/02/13)

SnCl4- and TiCl4-catalyzed anomerization of acylated O - And S -glycosides: Analysis of factors that lead to higher α: β d reaction rates
The quantification of factors that influence both rates and stereoselectivity of anomerization reactions catalyzed by SnCl4 and TiCl4 and how this has informed the synthesis of α-O- and α-S-glycolipids is discussed. The SnCl4-catalyzed anomerization reactions of β-S- and β-O-glycosides of 18 substrates followed first order equilibrium kinetics and kf + kr values were obtained, where kf is the rate constant for the forward reaction (β → α) and kr is the rate constant for the reverse reaction (α → β). Comparison of the kf + k r values showed that reactions of glucuronic acid or galacturonic acid derivatives were ～10 to 3000 times faster than those of related glucoside and galactopyranoside counterparts and α:β ratios were generally also higher. Stereoelectronic effects contributed from galacto-configured compounds were up to 2-fold faster than those of corresponding glucosides. The introduction of groups, including protecting groups, which are increasingly electron releasing generally led to rate enhancements. The anomerization of S-glycosides was consistently faster than that of corresponding O-glycosides. Reactions were generally faster for reactions with TiCl4 than those with SnCl4. Anomeric ratios depended on the Lewis acid, the number equivalents of the Lewis acid, temperature, and substrate. Very high ratios of α-products for both O- and S-glucuronides were observed for reactions promoted by TiCl4; for these substrates TiCl4 was superior to SnCl4. Anomeric ratios from anomerization of S-glucosides were higher with SnCl4 than with TiCl4. The dependence of equilibrium ratio on Lewis acid and the number of equivalents of Lewis acid indicated that the equilibrium ratio is determined by a complex of the saccharide residue bound to the Lewis acid and not the free glycoside. The high α:β ratios observed for anomerization of both O- and S-glycuronic acids can be explained by coordination of the C-1 heteroatom and C-6 carbonyl group of the product to the Lewis acid, which would enhance the anomeric effect by increasing the electron-withdrawing ability of the anomeric substituent and lead to an increase in the proportion of the α-anomer. Such an observation would argue against the existence of a reverse anomeric effect. Support for a chelation-induced endocyclic cleavage mechanism for the anomerization is provided by the trapping of a key intermediate. The data herein will help predict the tendency of β-glycosides to undergo anomerization; this includes cases where 1,2-trans glycosides are initial products of glycosidation reactions catalyzed by TiCl4 or SnCl4.
Pilgrim, Wayne,Murphy, Paul V.
supporting information; experimental part
p. 6747 - 6755
(2010/12/25)