- Selective 6-O-Debenzylation of mono- and disaccharide derivatives using ZnCl2-Ac2O-HOAc
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Freshly fused ZnCl2 in Ac2O/HOAc at room temperature has been used for 6-O-debenzylation of mono- and disaccharide derivatives giving yields more than 80%. Notably, allyl, acetyl, benzoyl, tosyl, thiono groups are unaffected under th
- Yang, Guangbin,Ding, Xianglan,Kong, Fanzuo
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- 2-Diphenylphosphinonyl-acetyl as a Remote Directing Group for the Highly Stereoselective Synthesis of β-Glycosides
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The configuration of the anomeric glycosidic linkages is crucial for maintaining the biological functions and activities of carbohydrate molecules. However, their stereochemistry control in glycosylation represents one of the most challenging tasks in car
- Liu, Xianglai,Lin, Yetong,Liu, Ao,Sun, Qianhui,Sun, Huiyong,Xu, Peng,Li, Guolong,Song, Yingying,Xie, Weijia,Sun, Haopeng,Yu, Biao,Li, Wei
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supporting information
p. 443 - 452
(2021/12/27)
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- Synthesis and biological evaluation of 1,6-bis-triazole-2,3,4-tri-O-benzyl-α-D-glucopyranosides as a novel α-glucosidase inhibitor in the treatment of Type 2 diabetes
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A novel series of 1,6-bis-triazole-benzyl-α-glucoside derivatives (7a-7ee) were designed, synthesized and evaluated for inhibitory activity against α-glucosidase. Most of the synthesized compounds exhibited good activity with IC50 ranging from
- Athipornchai, Anan,Chaidam, Suksamran,Saeeng, Rungnapha,Saehlim, Natthiya,Sirion, Uthaiwan
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supporting information
(2021/08/27)
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- Rapid Synthesis of l-Idosyl Glycosyl Donors from α-Thioglucosides for the Preparation of Heparin Disaccharides
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A new methodology for the synthesis of the most challenging heparin building block has been developed. Orthogonally protected l-idosyl glycosyl donors were prepared by C5 epimerization of the corresponding thioglucosides using the hydroboration/oxidation method followed by a 4,6-acetal formation. The α-anomeric configuration was crucial, and the bulky C4 substituent was advantageous for the high l-ido diastereoselectivity. The 4,6-arylmethylene group proved to be a directing element in glycosylation, whereby stereoselective α-idosylation could be achieved by using idosyl donors without a C-2 participating group.
- Herczeg, Mihály,Demeter, Fruzsina,Balogh, Tímea,Kelemen, Viktor,Borbás, Anikó
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supporting information
p. 3312 - 3316
(2018/07/13)
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- Four Different Regioisomeric Polycarbonates Derived from One Natural Product, d -Glucose
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Strategies for the preparation of polycarbonates, derived from the natural product d-glucose, which have the potential to degrade back into their bioresorbable starting material and CO2, were developed. By employing established carbohydrate pro
- Lonnecker, Alexander T.,Lim, Young H.,Felder, Simcha E.,Besset, Céline J.,Wooley, Karen L.
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p. 7857 - 7867
(2016/11/09)
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- Method for preventing cancer metastasis
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The present invention relates to the use of a specific family of glycerolipid compounds of formula (I) described in the detailed description or the manufacture of a medicament for the prevention or for the treatment of cancer metastasis.
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Page/Page column 20
(2015/11/10)
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- A novel selectfluor-mediated regioselective O-benzyl ether acetolysis of perbenzylated monosaccharides
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Selectfluor, a source of the super electrophile F+, has replaced conventional reagents that supply F+ for fluorination due to its attractive physical and chemical properties. This study is the first report of using Selectfluor as a d
- Tambie, Marlon S.,Jalsa, Nigel Kevin
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p. 545 - 559
(2016/04/19)
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- Regioselective acetolysis of highly O-benzylated carbohydrates promoted by iodine or an iodine/silane combined reagent: Use of isopropenyl acetate as an alternative to acetic anhydride
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Regioselective acetolytic de-O-benzylation of poly-O-benzylated sugars can be triggered by the activation of isopropenyl acetate (IPA) with either an iodine/silane combined reagent or iodine alone. Unlike other known acetolysis procedures, the protocols p
- Giordano, Maddalena,Iadonisi, Alfonso,Pastore, Antonello
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p. 3137 - 3147
(2013/06/27)
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- Impact of sugar stereochemistry on natural killer T cell stimulation by bacterial glycolipids
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Natural killer T (NKT) cells recognize glycolipids produced by Sphingomonas bacteria, and these glycolipids contain C6-oxidized sugars, either glucuronic acid or galacturonic acid, linked to ceramides. Glycolipids with gluco stereochemistry are the most p
- Deng, Shenglou,Mattner, Jochen,Zang, Zhuo,Bai, Li,Teyton, Luc,Bendelac, Albert,Savage, Paul B.
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supporting information; experimental part
p. 7659 - 7662
(2011/12/04)
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- Synthesis of potassium (2R)-2-O-α-d-glucopyranosyl-(1→6)-α-d-glucopyranosyl-2,3-dihydroxypropanoate a natural compatible solute
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Ethyl 6-O-acetyl-2,3,4-tribenzyl-1-thio-d-glucopyranoside, as a mixture of anomers, was employed for the stereoselective synthesis of the potassium salt of (2R)-2-O-α-d-glucopyranosyl-(1→6)-α-d-glucopyranosyl-2,3-dihydroxypropanoic acid (α-d-glucosyl-(1→6
- Lourenco, Eva C.,Maycock, Christopher D.,Rita Ventura
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experimental part
p. 2073 - 2078
(2010/03/01)
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- Indium(III) triflate: A highly efficient catalyst for reactions of sugars
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Indium(III) trifluoromethanesulfonate has been found to be extremely efficient in catalyzing acyl transfer reactions of various carbohydrates and their derivatives. Selective acetolyses of certain benzyl ethers/isopropylidene acetals of sugars have been possible using In(OTf)3 in Ac2O (neat). Reaction of the per-O-acetate of 2-deoxy-2-phthalimido-D-glucose with benzyl mercaptan in the presence of In(OTf)3 led to the formation of the corresponding thioglycoside in high yield. Facile formation and hydrolysis of the isopropylidene and benzylidene acetals of various carbohydrates have also been achieved very efficiently in the presence of In(OTf)3. The results show great promise for In(OTf)3 in synthetic carbohydrate chemistry.
- Giri, Santosh Kumar,Verma, Monika,Kartha, K. P. Ravindranathan
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experimental part
p. 464 - 478
(2009/04/06)
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- Stereoselective synthesis of branched cyclopentitols by titanium(III)-promoted reductive cyclization of 4-oxiranylaldehydes and 4-oxiranyl ketones derived from hexoses
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Titanocene chloride efficiently promotes the intramolecular reductive cross coupling of highly functionalized 4-oxiranyl-aldehydes and 4-oxiranyl ketones derived from readily available hexoses affording branched cyclopentitols with good stereoselectivity.
- Chiara, Jose Luis,Bobo, Sofia,Sesmilo, Esther
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experimental part
p. 3160 - 3166
(2009/04/06)
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- Synthesis of septanosides through an oxyglycal route
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(Chemical Equation Presented) A new route to synthesize septanoside derivatives from protected 2-hydroxyglycals is reported. Ring expansion of a pyranoside to a septanoside was achieved through key reactions of a cyclopropanation, ring opening, oxidation,
- Vijaya Ganesh,Jayaraman
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p. 5500 - 5504
(2008/02/09)
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- Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols
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A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely α-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by 3JC,H coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective.
- Namme, Rie,Mitsugi, Takashi,Takahashi, Hideyo,Shiro, Moto,Ikegami, Shiro
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p. 9183 - 9192
(2007/10/03)
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- Facile and regioselective preparation of partly O-benzylated d-glucopyranose acetates via acid-mediated simultaneous debenzylation-acetolysis
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Fully O-benzylated methyl α-d-glucopyranoside shows a steady order in stepwise debenzylation when it is treated with sulfuric acid in acetic anhydride. Based on the order of debenzylation, regioselective preparations of 2,3,4-tri-, 2,3-, 2,4-, 3,4-di-, an
- Cao, Yang,Okada, Yasunori,Yamada, Hidetoshi
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p. 2219 - 2223
(2007/10/03)
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- A one-pot selective deprotective acetylation of benzyl ethers and OTBDMS ethers using the BF3·Et2O-NaI-Ac2O reagent system
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An efficient selective deprotection followed by acetylation of several benzyl ethers, including 6-OBn ethers of monosaccharides, and -OTBDMS ethers has been developed by using the BF3·Et2O-NaI-Ac2O reagent system. In addition, both benzylidene and isopropylidene groups are deprotected to form the corresponding diacetates.
- Brar, Anita,Vankar, Yashwant D.
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p. 5207 - 5210
(2007/10/03)
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- Corrected order in the simultaneous debenzylation-acetolysis of methyl 2,3,4,6-tetra-O-benzyl-α-d-glucopyranoside
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The benzyl groups of methyl 2,3,4,6-tetra-O-benzyl-α-d-glucopyranoside were cleaved in the order of 6-O-Bn > 3-O-Bn > 4-O-Bn > 2-O-Bn under acid-mediated conditions in acetic anhydride. The order is a correction of that previously reported.
- Cao, Yang,Yamada, Hidetoshi
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p. 909 - 911
(2007/10/03)
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- A short access to the macrocyclic core of cycloviracin and glucolipsin
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The macrocyclic core of cycloviracin and glucolipsin has been synthesised in ten steps from levoglucosan and (S)-(-)-dimethyl malate. The limited number of steps to obtain this macrolide makes it a valuable procedure for the synthesis of analogues of cycl
- Bailliez, Vincent,Figueiredo, Renata M. de,Olesker, Alain,Cleophax, Jeannine
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p. 9151 - 9154
(2007/10/03)
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- Structure Assignment, Total Synthesis, and Antiviral Evaluation of Cycloviracin B1
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The first total synthesis of the antivirally active glycolipid cycloviracin B1 (1) is described. The approach is based on a two-directional synthesis strategy which constructs the C 2-symmetrical macrodiolide core of the target by an
- Fuerstner, Alois,Albert, Martin,Mlynarski, Jacek,Matheu, Maribel,DeClercq, Erik
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p. 13132 - 13142
(2007/10/03)
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- Solution-Phase Hexasaccharide Synthesis Using Glucosyl Iodides
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(Equation Presented) Oligosaccharides composed of 1,6-glucosyl residues have been prepared from glucosyl iodides. The reactions are highly stereoselective, giving the α-glycosides as the only isolated products in yields ranging from 84% to 94%. Oligomer s
- Lam, Son N.,Gervay-Hague, Jacquelyn
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p. 2039 - 2042
(2007/10/03)
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- Sc(OTf)3-catalyzed acetolysis of 1,6-anhydro-β-hexopyranoses and solvent-free per-acetylation of hexoses
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Acetolysis of 1,6-anhydro-β-hexopyranoses and solvent-free per-acetylation of hexoses with acetic anhydride at room temperature in excellent yields employing 0.5 mol% scandium(III) trifluoromethanesulfonate as an extremely efficient catalyst are, respectively, described here.
- Lee, Jinq-Chyi,Tai, Cheng-An,Hung, Shang-Cheng
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p. 851 - 855
(2007/10/03)
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- A concise synthesis of the fully functional lactide core of cycloviracin B with implications for the structural assignment of related glycolipids
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The absolute stereochemistry at the site of attachment of the fatty acid residues to the lactide core of the glycolipids cycloviracin B1 (1) and glucolipsin A (13) has been elucidated as (3R,3-R) by comparison of their 13C NMR data w
- Fuerstner, Alois,Albert, Martin,Mlynarski, Jacek,Matheu, Maribel
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p. 1168 - 1169
(2007/10/03)
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- Solution- and solid-phase oligosaccharide synthesis using glucosyl iodides: a comparative study
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Glycosyl iodide donors have been used in both solid- and solution-phase syntheses yielding α-(1->6)-linked glucosyl oligomers in highly efficient protocols. While the solid-phase strategy offers advantages in terms of ease of purification, it requires a t
- Lam, Son N.,Gervay-Hague, Jacquelyn
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p. 1952 - 1966
(2007/10/03)
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- Synthesis of artificial glycoconjugate polymers carrying 6-O-phosphocholine α-D-glucopyranoside, biologically active segment of main cell membrane glycolipids of Mycoplasma fermentans
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As carbohydrate probes to investigate the biological activity of novel phosphocholine-containing glycoglycerolipids of M. fermentans, artificial glycoconjugate polymers carrying 6-O-phosphocholine α-D-glucopyranoside were synthesized. The synthesis involved α-selective 1-O-p-nitrophenylation (pNP) of 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose in the presence of a Lewis acid followed by the introduction of a phosphocholine group at position O-6 by an amidite method. The pNP group was converted into a p-N-methacrylamidophenyl group for subsequent radical polymerization.
- Nishida, Yoshihiro,Takamori, Yusuke,Matsuda, Kazuhiro,Ohrui, Hiroshi,Yamada, Takeshi,Kobayashi, Kazukiyo
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p. 985 - 997
(2007/10/03)
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- A facile regioselective 1,6-O-diacetylation method of methyl- glycopyranosides and their dimethyl phosphonates
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A general method of 1,6-di-O-acetylation of methyl-α/β- glycopyranosides and a strategy to synthesize protected dimethyl (2,3,4-tri- O-benzyl-α-D-glycosyl) phosphonate having a free OH at C-6 are reported.
- Zhang, Guang-Tao,Guo, Zhong-Wu,Hui, Yong-Zheng
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p. 1907 - 1917
(2007/10/03)
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- Enolic ortho esters. VI* A new 'pyranose → cyclohexane' transformation via 1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-D-xylo-hex-5-enopyranose
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Hydrolysis of methyl 6-chloro-6-deoxy-2,3,4-tri-O-methyl-α-D-glucopyranoside (19b) and Swern oxidation of the resulting anomeric hemiacetals (20) gave 6-chloro-6-deoxy-2,3,4-tri-O-methyl-D-glucono-1,5-lactone (21), treatment of which with 1,2-bis(trimethylsilyloxy)ethane in the presence of trimethylsilyl trifluoromethanesulfonate gave 6-chloro-1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-D-glucopyranose (23a). Conversion of (23a) into the corresponding 6-iodo compound (23b) and treatment of this with 1,8-diazabicyclo[5.4.0]undec-7-ene afforded the enolic ortho ester 1,6-dideoxy-1,1-ethylenedioxy-2,3,4-triO-methyl-D-xylo-hex-5-enopyranose (26). Reaction of (26) with methylmagnesium iodide, or with titanium tetrachloride, gave (1R,6S,7R,8R,9S)-7,8,9-trimethoxy-6-methyl-2,5-dioxabicyclo[4.3.1]decan-1-ol (34), or (2S,3R,4R)-5,5-ethylenedioxy-2,3,4-trimethoxycyclohexanone (28), respectively.
- Bourke, David G.,Collins, David J.,Hibberd, Angus I.,McLeod, Malcolm D.
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p. 425 - 434
(2007/10/03)
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- Synthesis of Phosphatidyl-6-D-glucose and Attempted Synthesis of Phosphatidyl-1-D-glucose
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The synthesis of significant quantities of 6-O-(1',2'-di-O-palmitoyl-sn-glycero-3'-phosphoryl)-D-glucose, as its calcium and sodium salts, has been achieved by two procedures, both of which are based on the cyclic enediol phosphoryl method of phosphodiest
- Ramirez, Fausto,Mandal, Sukhendu B.,Marecek, James F.
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p. 2008 - 2013
(2007/10/02)
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- The Stereoselective Dehydrative α-Glucosylation Using 6-O-Acetyl- and 6-O-p-Nitrobenzoyl-2,3,4-tri-O-benzyl-D-glucopyranoses
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The stereoselective synthesis of α-linked glucobiose derivatives using 6-O-acetyl- or 6-O-p-nitrobenzoyl-2,3,4-tri-O-benzyl-D-glucopyranose and a ternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine in dichloromethane is described.
- Koto, Shinkiti,Morishima, Naohiko,Kihara, Yasuhiro,Suzuki, Hideko,Kosugi, Shigeharu,Zen, Shonosuke
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p. 188 - 191
(2007/10/02)
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- Bausteine von Oligosacchariden, XXX. Neue effektive β-Glycosidsynthese fuer Mannose-Glycoside. Synthesen von Mannose-haltigen Oligosacchariden
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A new method was developed for the stereo selective synthesis of oligosaccharides containing a β-linked mannose-unit which were hitherto not available by direct synthesis.The glycoside synthesis is promoted by a silversilicate-catalyst which was precipita
- Paulsen, Hans,Lockhoff, Oswald
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p. 3102 - 3114
(2007/10/02)
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