50605-13-5

Basic information

• Product Name: benzyl 2-(acetylamino)-3-O-benzyl-2-deoxy-4,6-O-(1-methylethylidene)hexopyranoside
• CAS NO: 50605-13-5
• Molecular Formula: C₂₅H₃₁NO₆
• Molecular Weight: 441.5167
• Mol File: 50605-13-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 604.2°C at 760 mmHg
• Flash Point: 319.2°C
• Density: 1.21g/cm³
• Vapor Pressure: 1.51E-14mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: benzyl 2-(acetylamino)-3-O-benzyl-2-deoxy-4,6-O-(1-methylethylidene)hexopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 2-(acetylamino)-3-O-benzyl-2-deoxy-4,6-O-(1-methylethylidene)hexopyranoside(50605-13-5)
• EPA Substance Registry System: benzyl 2-(acetylamino)-3-O-benzyl-2-deoxy-4,6-O-(1-methylethylidene)hexopyranoside(50605-13-5)

Safety Data

• Hazardous Substances Data: 50605-13-5(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 50605-12-4 benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 
• 58871-07-1 3-O-benzyl-4,6-O-isopropylidene-D-arabino-hex-1-enitol 
• 13435-12-6 N-Trimethylsilylacetamide 
• 100-51-6 benzyl alcohol 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 5432-46-2 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride 
• 10375-65-2 Acetic acid (2R,3S,4R,5R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-benzyloxy-tetrahydro-pyran-4-yl ester 
• 3055-51-4 benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 10375-65-2 benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 

Downstream Products

• 14855-31-3 benzyl 2-acetamido-3-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 62867-63-4 benzyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-β-D-glucopyranoside 
• 122351-24-0 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 4-(dibenzyl phosphate) 
• 13347-90-5 benzyl 3,4,6-tri-O-acetyl-2-(chloroacetylylamino)-2-deoxy-β-D-glucopyranoside 

Relevant articles and documents

Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs

Lipo-chitotetrasaccharide analogues where one central GlcNAc residue was replaced by a triazole unit have been synthesized from a derivative obtained by chitin depolymerization and a functionalized N-acetyl-glucosamine via the copper-catalyzed azide-alkyn

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.