144685-11-0

Basic information

• Product Name: Methyl 2-Acetamido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside
• Synonyms: Methyl 2-Acetamido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside;N-[5-hydroxy-2-methoxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS NO: 144685-11-0
• Molecular Formula: C₂₃H₂₉NO₆
• Molecular Weight: 415.47946
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 144685-11-0.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Solubility: Water
• CAS DataBase Reference: Methyl 2-Acetamido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-Acetamido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside(144685-11-0)
• EPA Substance Registry System: Methyl 2-Acetamido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside(144685-11-0)

Safety Data

• Hazardous Substances Data: 144685-11-0(Hazardous Substances Data)

Usage

Uses

Methyl 2-Acetamido-2-deoxy-3,6-di-O-benzyl-β-D-glucopyranoside is a reactant used in the preparation of 2-acetamido-2,4-dideoxy-β-D-xylo-hexopyranoside as inhitors of cell-surface glycosaminoglycan biosynthesis.

Upstream product

• 142560-73-4 methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 

Downstream Products

• 144685-23-4 methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3,4-tri-O-acetyl-6-deoxy-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 1415117-99-5 Glc beta-1-4 Glc beta 1-4-(3,6-dibenzyl)-N-acetylglucosamine 
• 144685-18-7 methyl 2-acetamido-3,6-di-O-benzyl-4-O-<4,6-O-benzylidene-3-O-phenoxythiocarbonyl-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl>-2-deoxy-β-D-glucopyranoside 
• 144685-16-5 methyl 2-acetamido-4-O-<3-O-benzoyl-4,6-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl>-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 144685-27-8 methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-<3,6-di-O-benzyl-4-deoxy-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside 
• 144685-17-6 methyl 2-acetamido-3,6-di-O-benzyl-4-O-<4,6-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl>-2-deoxy-β-D-glucopyranoside 
• 144685-21-2 methyl 2-acetamido-4-O-<3-O-benzoyl-4,6-O-benzylidene-2-O-(2,4-di-O-benzyl-3,6-dideoxy-α-L-xylo-hexopyranosyl)-β-D-galactopyranosyl>-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 144685-22-3 methyl 2-acetamido-4-O-<3-O-benzoyl-4,6-O-benzylidene-2-O-(2,3-di-O-benzyl-4,6-dideoxy-α-L-xylo-hexopyranosyl)-β-D-galactopyranosyl>-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 144685-19-8 methyl 2-acetamido-3,6-di-O-benzyl-4-O-<4,6-O-benzylidene-3-deoxy-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-xylo-hexopyranosyl>-2-deoxy-β-D-glucopyranoside 
• 144685-29-0 methyl 2-acetamido-3,6-di-O-benzyl-4-O-<3,4-O-benzylidene-6-deoxy-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl>-2-deoxy-β-D-glucopyranoside 
• 144685-20-1 methyl 2-acetamido-3,6-di-O-benzyl-4-O-<4,6-O-benzylidene-2-O-(2,6-dideoxy-α-L-lyxo-hexopyranosyl)-β-D-galactopyranosyl>-2-deoxy-β-D-glucopyranoside 
• 144685-15-4 methyl 2-acetamido-4-O-(3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 144685-14-3 methyl 2-acetamido-3,6-di-O-benzyl-4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside 
• 144685-25-6 methyl 2-acetamido-3,6-di-O-benzyl-4-O-(3,4-O-benzylidene-6-deoxy-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside 

Relevant articles and documents

Synthesis of methyl 5a′-carba-β-lactoside and N-acetyl-5a′-carba-β-lactosaminides, and related 5a′-carbadisaccharides

Construction of the ether-linked methyl 5a′-carba-β-lactoside (3) and N-acetyl-5a′-carba-β-lactosaminide (4) were carried out starting from the coupling products 15 and 16, readily obtained by coupling between 1,2-anhydro-4,6-O-benzylidene-5a-carba-D-mannopyranose (7) and the oxide anions generated from methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (8) and methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (10), respectively. Their 5a-carba-α-D-mannopyranose moieties were transformed into those of 5a-carba-β-D-galactopyranose by a sequence of reaction: Oxidation of the 2′-OH group, epimerization of the C-1′ with DBU, selective reduction of the carbonyl group, and epimerization of the C-4′ via oxidation and then reduction of 4′-OH or SN2 reaction of the 4′-mesylate with an acetate anion. Reaction of 1,2-anhydro-6-O-benzyl-3,4-O-isopropylidene-5a-carba-α-D-galactopyranose (6), initially expected as the potential donor, with these oxide anions did not give any ether-linked products, rather resulting in elimination reaction of 7. However, coupling of the epoxide 6 with methyl 2-acetamido-4-amino-2,4-dideoxy-β-D-glucopyranosides (19) easily gave rise to imino-linked 5a′-carbadisaccharide derivative 38, which, after deprotection, gave the imino-linked congener 5. On the other hand, two biologically interesting carbadisaccharides including methyl N,N′-diacetyl-5a′-carbachitobioside (45) were obtained from the versatile intermediate 24.