367946-92-7

Upstream product

• 214333-67-2 (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)methylene acetate 
• 75-65-0 tert-butyl alcohol 
• 367947-02-2 2,4-dinitro-6-(methoxycarbonyl)phenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 838888-66-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl N-trichloroacetylcarbamate 
• 604-69-3 β-D-glucose pentaacetate 
• 194088-16-9 1-O-propargyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 214333-70-7 2-oxopropyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 34272-02-1 1-O-propargyl 2,3,4,6-tetra-O-acetyl-β-D-glucose 
• 34272-03-2 propargyl β-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 208466-14-2 Phosphorous acid dimethyl ester (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 104550-44-9 1-O-mesyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose 

Relevant academic research and scientific papers

Electrochemical Glycosylation Method

Hydroxyl-protected and -unprotected glycosyl aryloxides react with alcohols under mild electrolytic conditions to give the corresponding glycosides.

Catalytic and stereoselective glycosylation with glycosyl N-trichloroacetylcarbamate

Catalytic and stereoselective glycosylation efficiently proceeded by activating a glycosyl N-trichloroacetylcarbamate with a catalytic amount of Lewis acids in the presence of a glycosyl acceptor and molecular sieves 5 ?. Catalytic and one-pot dehydrative

Glycosyl trichloroacetylcarbamate: A new glycosyl donor for O-glycosylation

Glycosyl trichloroacetylcarbamates, readily obtained by reacting 1-hydroxy sugars with trichloroacetylisocyanate, have been found as excellent glycosyl donors, and the corresponding O-glycosides are formed in good to excellent yields with a fairly good degree of selectivity.

Generation of alkoxycarbenium ion pools from thioacetals and applications to glycosylation chemistry

(Chemical Equation Presented) Alkoxycarbenium ions have been generated and accumulated as "cation pools" by the low-temperature electrochemical oxidation of α-phenylthioethers. Although an unsuccessful attempt to accumulate glycosyl cations was made, a one-pot method for electrochemical glycosylation, which involves anodic oxidation of thioglycosides to generate glycosyl cation equivalents followed by their reactions with glycosyl acceptors, has been developed.

A new, efficient glycosylation method for oligosaccharide synthesis under neutral conditions: Preparation and use of new DISAL donors

Efficient, stereoselective glycosylation methods are required for the synthesis of complex oligosaccharides as tools in glycobiology. All glycosylation methods, which have found wide acceptance, rely on Lewis acid activation of glycosyl donors prior to glycosylation. Here, we present a new and efficient method for glycosylation under neutral or mildly basic conditions. Glycosides of methyl 2-hydroxy-3,5-dinitrobenzoate (DISAL) and its para regioisomer, methyl 4-hydroxy-3,5-dinitrobenzoate, were prepared by nucleophilic aromatic substitution. In a first demonstration of their potential as glycosyl donors, stereospecific glycosylation of methanol was achieved. In the glycosylation of more hindered alcohols, the β-donor proved more reactive, and α-glucosides were predominantly formed. Glycosylation of protected monosaccharides, with free 6-0H or 3-OH, proceeded smoothly in 1-methyl-2-pyrrolidinone (NMP) at 40-60 °C in the absence of Lewis acids and bases in good to excellent yields. Glycosylation of 3-OH gave the α-linked disaccharide only.

Design, development and utility of glycosyl donors bearing an acetoxymethoxy leaving group

Novel glycosyl donors 2d, 4d and 6d bearing an 'acetoxy methoxy' leaving group have been prepared and their utility is shown by coupling them with alcohols A-G to obtain di- and trisaccharides by use of BF3-Et2O as a promoter.

GLYCOSYLATION USING GLYCOSYL PHOSPHITE AS A GLYCOSYL DONOR

Glycosylation using glycosyl phosphites as glycosyl donors in the presence of a Lewis acid such as ZnCl2 or ZnCl2-AgClO4 has afforded the glycosides including sialoglycosides in good yields.