131204-11-0

Basic information

• Product Name: 3,4,6-tri-O-acetyl-α-D-glucopyranose 1,2-< orthoacetate>
• Synonyms: 3,4,6-tri-O-acetyl-α-D-glucopyranose 1,2-< orthoacetate>
• CAS NO: 131204-11-0
• Molecular Weight: 1011.98
• Mol File: 131204-11-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3,4,6-tri-O-acetyl-α-D-glucopyranose 1,2-< orthoacetate>(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,6-tri-O-acetyl-α-D-glucopyranose 1,2-< orthoacetate>(131204-11-0)
• EPA Substance Registry System: 3,4,6-tri-O-acetyl-α-D-glucopyranose 1,2-< orthoacetate>(131204-11-0)

Safety Data

• Hazardous Substances Data: 131204-11-0(Hazardous Substances Data)

Upstream product

• 54400-75-8 allyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 65730-00-9 allyl 2-acetamido-3-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 131204-07-4 allyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-(4-methoxybenzyl)-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 131204-04-1 allyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside 
• 131204-05-2 allyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranoside 
• 131204-03-0 allyl 2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 131204-08-5 allyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 131204-12-1 α-D-glucopyranose 1,2-< orthoacetate> 

Relevant articles and documents

Synthesis of a tri- and a tetra-saccharide fragment of the capsular polysaccharide of type III group B Streptococcus.

Syntheses of the propyl glycosides (1-3) of beta-D-Galp-(1----4)-beta-D-GlcpNAc, beta-D-Glcp-(1----6)-[beta-D-Galp-(1----4)]-beta-D-GlcpNAc, and beta-D-Galp-(1----4)-beta-D-Glcp-(1----6)-[beta-D-Galp-(1----)]-beta-D- GlcpNAc, respectively, are reported. Reaction of allyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-(4-methoxybenzyl)-beta-D-glucopyranos ide with 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide under Hg(CN)2 catalysis, followed by oxidative removal of the 4-methoxybenzyl group, gave allyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-beta-D- galactopyranosyl)-beta-D-glucopyranoside (10) O-deacetylation of which, followed by hydrogenolysis/hydrogenation, gave 1. Reaction of 10 with beta-D-glucopyranose penta-acetate and beta-lactose octa-acetate, under catalysis by trimethylsilyl trifluoromethanesulfonate, and treatment of the products as for 10 gave 2 and 3, respectively. Attempted glycosylation of 10 with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl bromide under catalysis by Hg(CN)2 or silver trifluoromethanesulfonate gave an orthoester. Complete assignments of the 1H- and 13C-n.m.r. spectra of 1-3 are reported together with their carbon spin-lattice relaxation times which indicate that 3 assumes a compact instead of an extended shape.