85193-92-6

Upstream product

• 69892-42-8 methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 144789-65-1 methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 6619-04-1 N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide 
• 100-44-7 benzyl chloride 
• 354986-43-9 methyl N,N-diacetyl-2-amino-2-deoxy-4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 6619-02-9 methyl N-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 

Downstream Products

• 85193-93-7 methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranoside 
• 290819-83-9 methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-mesyl-α-D-glucopyranoside 
• 155500-95-1 methyl 2-acetamido-3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside 
• 290819-88-4 methyl 2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-4-fluoro-α-D-galactopyranoside 
• 85193-94-8 methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-β-D-galactopyranosyl-α-D-glucopyranoside 
• 1253183-68-4 methyl [2-O-benzoyl-3-O-benzyl-6-O-chloroacetyl-4-O-(1-naphthylmethyl)-β-D-glucopyranosyl]-(1->4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside) 
• 144789-65-1 methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 

Relevant academic research and scientific papers

A 1-acetamido derivative of 6-epi-valienamine: An inhibitor of a diverse group of β-N-acetylglucosaminidases

The synthesis of an analogue of 6-epi-valienamine bearing an acetamido group and its characterisation as an inhibitor of β-N- acetylglucosaminidases are described. The compound is a good inhibitor of both human O-GlcNAcase and human β-hexosaminidase, as well as two bacterial β-N-acetylglucosaminidases. A 3-D structure of the complex of Bacteroides thetaiotaomicron BtGH84 with the inhibitor shows the unsaturated ring is surprisingly distorted away from its favoured solution phase conformation and reveals potential for improved inhibitor potency. This journal is The Royal Society of Chemistry.

Why are the hydroxy groups of partially protected N-acetylglucosamine derivatives such poor glycosyl acceptors, and what can be done about it? A comparative study of the reactivity of N-acetyl-, N-phthalimido-, and 2-azido-2-deoxy-glucosamine derivatives

Competition experiments were used to determine that the 4-OH of a 2-deoxy-2-azidoglucose derivative is more reactive than that of the corresponding N-phthalimido glucose derivative which, in turn, is more easily glycosylated than the N-acetyl derivative.

DISAL glycosyl donors for efficient glycosylations under acidic conditions: Application to solid-phase oligosaccharide synthesis

The use of DISAL (methyl dinitrosalicylate) glycosyl donors in efficient Lewis acid-promoted glycosylations is reported. N-Acetyl-D-glucosamine monosaccharide acceptors are successfully glycosylated at O-6 or O-4 using benzyl- and benzoyl-protected DISAL donors in CH2Cl2 or nitromethane in the presence of LiClO4. The resultant disaccharides are isolated in yields ranging from 35 to 93%. Other Lewis acids such as FeCl3, TMSOTf, or BF3·Et2O also prove efficient for glycosylation of the secondary alcohol cyclohexanol. However, for the synthesis of disaccharides, the mild activation by LiClO4 gives higher yields. This approach is extended to efficient solid-phase glycosylation of a D-glucosamine derivative anchored by the 2-amino group through a Backbone Amide Linker (BAL) to a polystyrene support.

SYNTHESIS OF p-NITROPHENYL 2-ACETAMIDO-2-DEOXY-4-O-β-D-GALACTOPYRANOSYL-β-D-GLUCOPYRANOSIDE, AND p-NITROPHENYL 6-O-(2-ACETAMIDO-2-DEOXY-3-O- AND -4-O-β-D-GALCTOPYRANOSYL-β-D-GLUCOPYRANOSYL)-α-D-MANNOPYRANOSIDE

A facile synthesis of p-nitrophenyl 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-β-D-glucopyranoside was accomplished by saponification of the product obtained by reaction of 2-acetamido-3,6-di-O-acetyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyran