50605-12-4

Basic information

• Product Name: Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-b-D-glucopyranoside
• Synonyms: Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-b-D-glucopyranoside;PhenylMethyl 2-(AcetylaMino)-2-deoxy-4,6-O-(1-Methylethylidene)-β-D-glucopyranoside, BADIG;Benzyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-beta-D-glucopyranoside, Benzyl 4,6-O-isopropylidene-beta-GlcNAc, BADIG;Benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-beta-D-glucopyranoside min. 98%;Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-2-D-glucopyranoside
• CAS NO: 50605-12-4
• Molecular Formula: C₁₈H₂₅NO₆
• Molecular Weight: 351.397
• Product Categories: Carbohydrates & Derivatives
• Mol File: 50605-12-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 173.5-175.5°C
• Boiling Point: 567.57 °C at 760 mmHg
• Flash Point: 297.056 °C
• Appearance: /
• Density: 1.259 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.561
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-b-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-b-D-glucopyranoside(50605-12-4)
• EPA Substance Registry System: Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-b-D-glucopyranoside(50605-12-4)

Safety Data

• Hazardous Substances Data: 50605-12-4(Hazardous Substances Data)

Usage

Uses

An intermediate in the synthesis of Lipid A, which is known to be responsible for most of the biological activities of the lipopolysaccharide of gram-negative bacteria

InChI:InChI=1/C18H25NO6/c1-11(20)19-14-15(21)16-13(10-23-18(2,3)25-16)24-17(14)22-9-12-7-5-4-6-8-12/h4-8,13-17,21H,9-10H2,1-3H3,(H,19,20)/t13?,14-,15+,16+,17+/m0/s1

Upstream product

• 100-51-6 benzyl alcohol 
• 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 
• 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 
• 3055-51-4 benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside 
• 77-76-9 2,2-dimethoxy-propane 
• 3055-51-4 benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside 

Downstream Products

• 80035-18-3 benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 1442643-80-2 C₁₉H₂₉NO₁₀*ClH 
• 130541-80-9 benzyl O-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 
• 1442643-71-1 C₂₂H₃₃NO₁₀ 
• 122351-24-0 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 4-(dibenzyl phosphate) 
• 62867-63-4 benzyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-β-D-glucopyranoside 
• 14855-31-3 benzyl 2-acetamido-3-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 80035-19-4 benzyl 2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-β-D-glucopyranoside 
• 58902-39-9 benzyl 2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 104640-21-3 benzyl 2-deoxy-2-<(3S)-3-hydroxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside 
• 104640-20-2 benzyl 2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside 
• 104640-27-9 benzyl 2-deoxy-4-O-(O,O-diphenylphosphono)-3-O-tetradecanoyl-2-<(3R)-3-tetradecanoyloxytetradecanamido>-β-D-glucopyranoside 
• 104712-61-0 benzyl 2-deoxy-4-O-(O,O-diphenylphosphono)-3-O-tetradecanoyl-2-<(3S)-3-tetradecanoyloxytetradecanamido>-β-D-glucopyranoside 
• 104640-24-6 benzyl 2-deoxy-3-O-tetradecanoyl-2-<(3R)-3-tetradecanoyloxytetradecanamido>-6-O-trityl-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.