- 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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- 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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- 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 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- 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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- 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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- 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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- 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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p. 6725 - 6728
(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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- 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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