75336-67-3

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 75336-64-0 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-chloro-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 75336-63-9 methyl <2,3,4-tri-O-benzyl-α-D-glucopyranosyl chloride>uronate 
• 75336-65-1 methyl 2,3,4-tri-O-benzyl-α-D-glucopyranuronate 
• 1163254-57-6 C₃₄H₃₄O₆S 

Relevant academic research and scientific papers

A "traceless" Directing Group Enables Catalytic SN2 Glycosylation toward 1,2- cis-Glycopyranosides

Generally applicable and stereoselective formation of 1,2-cis-glycopyranosidic linkage remains a long sought after yet unmet goal in carbohydrate chemistry. This work advances a strategy to this challenge via stereoinversion at the anomeric position of 1,2-trans glycosyl ester donors. This SN2 glycosylation is enabled under gold catalysis by an oxazole-based directing group optimally tethered to a leaving group and achieved under mild catalytic conditions, in mostly excellent yields, and with good to outstanding selectivities. The strategy is also applied to the synthesis of oligosaccharides.

Stereodirecting effect of the pyranosyl C-5 substituent in glycosylation reactions

(Chemical Equation Presented) The stereodirecting effect of the glycosyl C-5 substituent has been investigated in a series of D-pyranosyl thioglycoside donors and related to their preferred positions in the intermediate 3H4 and

A Rapid and Efficient Synthesis of 1,2-trans-β-Linked Glycosides via Benzyl- or Benzoyl-protected Glycopyranosyl Phosphates

A highly stereocontrolled construction of 1,2-trans-β-glycosidic linkage with or without neighbouring-group participation has been achieved using benzyl- or benzoyl-protected glycopyranosyl phosphates as glycosyl donors in the presence of trimethylsilyl t

Stereoselective glycosidations of uronic acids

Stereoselective glycosidation and disaccharide formation of uronic acids were performed with silver perchlorate in acetonitrile. The course of the reaction is controlled by intermediate nitrilium acetonitrile conjugates, which are generated in situ.