179072-65-2

Upstream product

• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 10257-28-0 D-Galactose 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 25878-60-8 D-galactose pentaacetate 
• 179072-63-0 phenyl 3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside 
• 819798-47-5 phenyl 2,4,6-tri-O-benzyl-3-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 179072-66-3 phenyl 2,4,6-tri-O-benzyl-3-O-chloroacetyl-1-thio-β-D-galactopyranoside 
• 273408-93-8 (2R,3S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-4-one 

Relevant academic research and scientific papers

Directing effect by remote electron-withdrawing protecting groups at O-3 or O-4 position of donors in glucosylations and galactosylations

Glucosylations and galactosylations of various acceptors with donors possessing an electron-withdrawing benzylsulfonyl, benzoyl, or acetyl group at the O-3 or O-4 position were performed. A β-directing effect by the benzylsulfonyl group at O-3 of the glucosyl donors and by the benzylsulfonyl and acyl groups at O-4 of the glucosyl donors was observed. In contrast, acyl groups at O-3 of the glucosyl donors and acyl groups at O-3 and O-4 of the galactosyl donors exhibited an α-directing effect. The α-directing effect is partly considered to remote participation of the acyl groups, whereas the β-directing effect is somewhat attributed to the SN2-like reaction of the acceptor with the glycosyl triflate or the contact ion pair, which is stabilized by remote electron-withdrawing groups. Further evidence for the stability of the α-glycosyl triflates was determined by a low-temperature NMR study.

Single-step multisyntheses of glycosyl acceptors: Benzylation of n-1 hydroxyl groups of phenylthio glycosides of xylose, mannose, glucose, galactose, 2-azido-2-deoxy-glucose, and 2-azido-2-deoxy-galactose

An array of synthons is required to access an oligosaccharide library; however, multistep and thus time-consuming synthesis is inevitable. To rapidly access such synthetic units, multiple benzylation reactions of monosaccharides under phase-transfer condi

Orthogonal glycosylation strategy in synthesis of extended blood group B determinant

The orthogonal glycosylation strategy was applied for the synthesis of extended blood type B determinant (2) of a novel glycolipid 1. Key features in the synthesis are 1) four monosaccharide units were synthesized as either glycosyl fluoride or thioglycoside to be engaged to the orthogonal glycosylation strategy and 2) all necessary manipulations were completed at the monosaccharide level, therefore, manipulations during the elongation of sugar chain were minimized.