62867-63-4

Basic information

• Product Name: BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE
• Synonyms: BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE;2-Acetamido-1,3,6-tri-O-benzyl-2-deoxy-b-D-glucopyranoside;b-D-Glucopyranoside, phenylMethyl 2-(acetylaMino)-2-deoxy-3,6-bis-O-(phenylMethyl)-
• CAS NO: 62867-63-4
• Molecular Formula: C₂₉H₃₃NO₆
• Molecular Weight: 491.57542
• Product Categories: Carbohydrates & Derivatives
• Mol File: 62867-63-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 173-174°C
• Boiling Point: 694.641°C at 760 mmHg
• Flash Point: 373.905°C
• Appearance: /
• Density: 1.234g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, Dichloromethane
• CAS DataBase Reference: BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(62867-63-4)
• EPA Substance Registry System: BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(62867-63-4)

Safety Data

• Hazardous Substances Data: 62867-63-4(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

InChI:InChI=1/C29H33NO6/c1-21(31)30-26-28(34-18-23-13-7-3-8-14-23)27(32)25(20-33-17-22-11-5-2-6-12-22)36-29(26)35-19-24-15-9-4-10-16-24/h2-16,25-29,32H,17-20H2,1H3,(H,30,31)/t25?,26-,27+,28+,29+/m0/s1

Upstream product

• 80035-36-5 benzyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside 
• 191482-37-8 benzyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 100-51-6 benzyl alcohol 
• 134308-75-1 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 868161-61-9 benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 3055-51-4 benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside 
• 5432-46-2 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 50605-12-4 benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 

Downstream Products

• 62867-64-5 benzyl 2-acetamido-4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 122351-24-0 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 4-(dibenzyl phosphate) 
• 86781-97-7 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside 
• 137105-34-1 N-[4-((2R,3S,4R,5R,6R)-5-Acetylamino-4,6-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxymethyl)-phenyl]-2,2-dimethyl-propionamide 
• 1287768-18-6 C₅₃H₅₄N₄O₁₄ 
• 1287768-41-5 C₅₆H₅₆N₄O₁₄ 
• 1287768-43-7 C₅₅H₅₈N₄O₁₅ 
• 1287768-44-8 C₃₆H₃₉N₇O₁₅ 
• 1287768-23-3 benzyl 2-acetamido-3,6-di-O-benzyl-4-O-propargyl-2-deoxy-β-D-glucopyranoside 
• 70209-54-0 Benzyl-2-acetamido-3,6-di-O-benzyl-2-desoxy-4-O-(β-D-galactopyranosyl)-α-D-glucopyranosid 
• 13347-90-5 benzyl 3,4,6-tri-O-acetyl-2-(chloroacetylylamino)-2-deoxy-β-D-glucopyranoside 

Relevant articles and documents

Efficient synthesis of meningococcal X polysaccharide repeating unit (n-acetylglucosamine-4-phosphate) as analytical standard for polysaccharide determination

Serogroup X Neisseria meningitidis (MenX) is emerging in many African countries as a major cause of meningococcal meningitis, but no preventative therapy against this serogroup is yet available. N-Acetylglucosamine-4-phosphate (4P-GlcNAc), the monomeric repeating unit of MenX polysaccharide, is an important requirement for the development of an analytical method specific for MenX polysaccharide quantification. At the moment, this compound is not commercially available. Herein an efficient preparation of this monosaccharide is reported.

Design and synthesis of unnatural heparosan and chondroitin building blocks

Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted

1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranose as a glycosyl donor in syntheses of oligosaccharides

1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranose was tested as a glycosyl donor for oligosaccharide synthesis via ferric chloride-catalyzed coupling reaction.Glycosyl acceptors tried (6 in all) were O-benzyl-protected D-galactosides having free OH groups at positions 3 and 4, respectively, and similarly protected glycosides of D-glucose and 2-acetamido-2-deoxy-D-glucose unsubstituted on O-4.Existing syntheses of all the acceptors were improved, in four instances by exploitation of Garegg and Hultberg's cyanoborohydride procedure for the conversion 4,6-O-benzylidene -> 6-O-benzyl .Good to excellent yields of β-linked disaccharides were obtained from the galactoside and glucoside acceptors, but with allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside, stereoselectivity was lost (α:β-ratio 1:2).Allyl and benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosides gave, respectively, the allyl and benzyl β-glycosides of the donor as major products.A mechanism is proposed for this transglycosidation reaction.The N-chloroacetyl groups in the disaccharide products were readily converted into N-acetyl by reduction with zinc-acetic acid.