- Synthesis of α-glycosyl thiols by stereospecific ring-opening of 1,6-anhydrosugars
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Treatment of 1,6-anhydrosugars with commercially available bis(trimethylsilyl) sulfide in the presence of trimethylsilyl triflate led to the formation of α-glycosyl thiols. All the reactions were highly stereoselective and afforded the α-glycosyl thiols in good to excellent yields. By this procedure, a variety of 1,6-anhydrosugars, differing in their sugar units, glycosidic linkages, and protecting group pattern, were converted smoothly into the corresponding α-glycosyl thiols, which could be of great utility in thioglycoside chemistry. It is noteworthy that 1,6-anhydrosugars carrying the 2-O-acyl group and 1,6-anhydrosugar-containing oligosaccharides could also be ring-opened stereospecifically under the same conditions to give rise to the corresponding 1-thiosugars in high yields. Thus, a very concise and efficient access to α-glycosyl thiols of great value was established (Figure presented).
- Zhu, Xiangming,Dere, Ravindra T.,Jiang, Junyan,Zhang, Lei,Wang, Xiaoxia
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experimental part
p. 10187 - 10197
(2012/02/05)
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- Synthesis of 1,6-anhydro sugars catalyzed by silica supported perchloric acid
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A new and efficient method for the preparation of 1,6-anhydro sugars using silica supported perchloric acid as a catalyst is described. The catalyst is heterogeneous and 1,6-anhydro sugars could be formed within a few minutes with good yields.
- Chun, Yuexing,Yan, Shiqiang,Li, Xiangpeng,Ding, Ning,Zhang, Wei,Wang, Peng,Li, Ming,Li, Yingxia
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experimental part
p. 6196 - 6198
(2011/12/01)
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- Alpha-GLYCOSYL THIOLS AND alpha-S-LINKED GLYCOLIPIDS
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The present invention relates to stereoselective methods for the preparation of α-glycosyl thiols and α-S-linked glycosylceramides.
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- Gold-catalyzed glycosidations: Synthesis of 1,6-anhydro saccharides
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Various 1,6-anhydro sugars are synthesized utilizing salient features of gold-catalyzed glycosidations. All the reactions occurred under mild conditions in the presence of 7 mol % of AuBr3 enabling easy synthesis of 1,6-anhydro sugars from corr
- Thadke, Shivaji A.,Hotha, Srinivas
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experimental part
p. 5912 - 5914
(2010/11/18)
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- The first synthesis of a thioglycoside analogue of the immunostimulant KRN7000
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(Chemical Equation Presented) The first total synthesis of a thioglycoside analogue of KRN7000, a potential immunostimulant, is described. Two key intermediates are α-galactosyl thiol 4 and phytosphingosine derivative 5, which were both prepared from D-galactose.
- Dere, Ravindra T.,Zhu, Xiangming
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supporting information; experimental part
p. 4641 - 4644
(2009/05/27)
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- Stereoselective total synthesis of the glycosyl phosphatidylinositol (GPI) anchor of Trypanosoma brucei
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The total synthesis of O--(1->2)-O-α-D-mannopyranosyl-(1->6)-O-6)-α-D-galactopyranosyl-(1->3)>-O-α-D-mannopyranosyl-(1->4)-2-amino-2-deoxy-α-D-glucopyranosyl>-(1->6)-1-O-(1,2-
- Murakata, Chikara,Ogawa, Tomoya
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- Bausteine von Oligosacchariden, XXIX. Synthese des Trisaccharids aus N-Acetylglucosamin, Galactose und Rhamnose einer O-determinanten Kette von Escherichia coli. Abhaengigkeit der Stereoselektivitaet der α-Glycosidsynthese von der Reaktivitaet des Pyranos
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The mercury salt catalysed reaction of substituted α-D-galactosyl halides with the reactive 4-OH groups of the rhamnosides 18 and 19 were studied.The order of reactivity of the halides increases with the following substituents: O-acetyl O-glucosyl O-b
- Paulsen, Hans,Lockhoff, Oswald
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p. 3079 - 3101
(2007/10/02)
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