65730-00-9

Basic information

• Product Name: Allyl 2-(Acetylamino)-2-deoxy-3-O-benzyl--D-glucopyranoside
• Synonyms: 2-Propenyl 2-(Acetylamino)-2-deoxy-3-O-(phenylmethyl)--D-glucopyranoside;2-Propenyl 2-(Acetylamino)-2-deoxy-3-O-benzyl--D-glucopyranoside;Allyl 2-(Acetylamino)-2-deoxy-3-O-benzyl--D-glucopyranoside;Allyl-2-acetamido-3-O-benzyl-2-deoxy-b-D-glucopyranose;Allyl 2-(Acetylamino)-2-deoxy-3-O-benzyl-2-D-glucopyranoside
• CAS NO: 65730-00-9
• Molecular Formula: C₁₈H₂₅NO₆
• Molecular Weight: 351.3942
• Product Categories: Carbohydrates & Derivatives
• Mol File: 65730-00-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 590.665 °C at 760 mmHg
• Flash Point: 311.023 °C
• Appearance: off-white solid
• Density: 1.237 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.561
• Solubility: Water
• CAS DataBase Reference: Allyl 2-(Acetylamino)-2-deoxy-3-O-benzyl--D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Allyl 2-(Acetylamino)-2-deoxy-3-O-benzyl--D-glucopyranoside(65730-00-9)
• EPA Substance Registry System: Allyl 2-(Acetylamino)-2-deoxy-3-O-benzyl--D-glucopyranoside(65730-00-9)

Safety Data

• Hazardous Substances Data: 65730-00-9(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

InChI:InChI=1/C18H25NO6/c1-3-9-23-18-15(19-12(2)21)17(16(22)14(10-20)25-18)24-11-13-7-5-4-6-8-13/h3-8,14-18,20,22H,1,9-11H2,2H3,(H,19,21)/t14?,15?,16-,17-,18-/m1/s1

Upstream product

• 131204-04-1 allyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside 
• 54400-75-8 allyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 131204-03-0 allyl 2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside 

Downstream Products

• 131204-06-3 allyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-(4-methoxybenzyl)-β-D-glucopyranoside 
• 131204-05-2 allyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranoside 
• 131204-12-1 α-D-glucopyranose 1,2-< orthoacetate> 
• 131204-09-6 allyl 2-acetamido-6-O-acetyl-3-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 131204-11-0 3,4,6-tri-O-acetyl-α-D-glucopyranose 1,2-< orthoacetate> 
• 399036-11-4 C₅₃H₅₂N₄O₁₆ 
• 399036-10-3 allyl O-(3-O-acetyl-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzoyl-3-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 399036-12-5 2-azidoethyl O-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzoyl-3-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 74352-48-0 allyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-tosyl-β-D-glucopyranoside 
• 399036-09-0 allyl 2-acetamido-6-O-benzoyl-3-O-benzyl-2-deoxy-β-D-glucopyranoside 

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.