29704-64-1Relevant academic research and scientific papers
Synthesis of α-glycosyl thiols by stereospecific ring-opening of 1,6-anhydrosugars
Zhu, Xiangming,Dere, Ravindra T.,Jiang, Junyan,Zhang, Lei,Wang, Xiaoxia
experimental part, p. 10187 - 10197 (2012/02/05)
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).
Synthesis of 1,6-anhydro sugars catalyzed by silica supported perchloric acid
Chun, Yuexing,Yan, Shiqiang,Li, Xiangpeng,Ding, Ning,Zhang, Wei,Wang, Peng,Li, Ming,Li, Yingxia
experimental part, p. 6196 - 6198 (2011/12/01)
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.
Gold-catalyzed glycosidations: Synthesis of 1,6-anhydro saccharides
Thadke, Shivaji A.,Hotha, Srinivas
experimental part, p. 5912 - 5914 (2010/11/18)
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
Alpha-GLYCOSYL THIOLS AND alpha-S-LINKED GLYCOLIPIDS
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Figure 1, (2010/08/07)
The present invention relates to stereoselective methods for the preparation of α-glycosyl thiols and α-S-linked glycosylceramides.
The first synthesis of a thioglycoside analogue of the immunostimulant KRN7000
Dere, Ravindra T.,Zhu, Xiangming
supporting information; experimental part, p. 4641 - 4644 (2009/05/27)
(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.
Stereoselective total synthesis of the glycosyl phosphatidylinositol (GPI) anchor of Trypanosoma brucei
Murakata, Chikara,Ogawa, Tomoya
, p. 95 - 114 (2007/10/02)
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-
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
Paulsen, Hans,Lockhoff, Oswald
, p. 3079 - 3101 (2007/10/02)
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
