1590392-16-7

Basic information

• Product Name: 4-O-(3,4,6-tri-O-benzyl-2-O-imidazoylsulfonyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal
• Synonyms: 4-O-(3,4,6-tri-O-benzyl-2-O-imidazoylsulfonyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal
• CAS NO: 1590392-16-7
• Molecular Weight: 869
• Mol File: 1590392-16-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-O-(3,4,6-tri-O-benzyl-2-O-imidazoylsulfonyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal(CAS DataBase Reference)
• NIST Chemistry Reference: 4-O-(3,4,6-tri-O-benzyl-2-O-imidazoylsulfonyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal(1590392-16-7)
• EPA Substance Registry System: 4-O-(3,4,6-tri-O-benzyl-2-O-imidazoylsulfonyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal(1590392-16-7)

Safety Data

• Hazardous Substances Data: 1590392-16-7(Hazardous Substances Data)

Upstream product

• 1590392-10-1 4-O-(6-O-benzyl-3,4-O-isopropylidene-2-O-p-methoxybenzyl-β-D-talopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal 
• 922520-80-7 4-O-[6-O-(1-methoxy-1-methylethyl)-3,4-O-isopropylidene-β-D-talopyranosyl]-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal 
• 1590392-12-3 C₃₅H₄₈O₁₂ 
• 1590392-15-6 4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal 
• 7189-69-7 N,N`-sulfuryldiimidazole 
• 1590392-14-5 4-O-(3,4,6-tri-O-benzyl-2-O-p-methoxybenzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal 
• 1590392-13-4 4-O-(3,6-di-O-benzyl-2-O-p-methoxybenzyl-β-D-mannopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal 
• 1590392-11-2 4-O-(3,6-di-O-benzyl-4-deoxy-2-O-p-methoxybenzyl-β-D-erhytrohex-4-enopyranosyl)-2,3:5,6-di-O-isopropylidenealdehydo-D-glucose dimethyl acetal 

Downstream Products

• 1590392-17-8 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 

Relevant articles and documents

Stereoselective synthesis of β-D-GlcNAc-(1→4)-D-Glc disaccharide starting from lactose

The stereoselective preparation of the β-D-GlcNAc-(1→4)-D-Glc disaccharide starting from known 4-O-[6-O-(1-methoxy-1-methylethyl)-3,4-O- isopropylidene-β-D-talopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D- glucose dimethyl acetal (2), in turn easily obtained from lactose, is reported. Key steps of this new procedure, that avoids the glycosylation reaction, are (a) a first epimerization at C-4' through an unusual procedure involving a completely stereospecific hydroboration-oxidation of the enol ether group of the hex-4-enopyranoside 4, obtained from 3 by base promoted acetone elimination, (b) an amination with inversion by S reaction on an imidazylate intermediate, and, finally, (c) N-acetylation followed by complete deprotection.