58794-70-0

Basic information

• Product Name: 1,2-O-isopropylidene-3,4,5,6-tetra-O-benzyl-D-sorbitol
• CAS NO: 58794-70-0
• Molecular Weight: 582.737
• Mol File: 58794-70-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,2-O-isopropylidene-3,4,5,6-tetra-O-benzyl-D-sorbitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-isopropylidene-3,4,5,6-tetra-O-benzyl-D-sorbitol(58794-70-0)
• EPA Substance Registry System: 1,2-O-isopropylidene-3,4,5,6-tetra-O-benzyl-D-sorbitol(58794-70-0)

Safety Data

• Hazardous Substances Data: 58794-70-0(Hazardous Substances Data)

Upstream product

• 53928-30-6 1,2-O-isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranoside 
• 135284-41-2 3,5,6-Tris-O-benzyl-D-sorbitol 
• 100-39-0 benzyl bromide 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 35958-64-6 3,5,6-Tri-O-benzyl-α,β-D-glucofuranose 
• 135284-42-3 (2S,3S,5R)-3,4,6-Tris-O-benzyl-1,2-O-isopropylidene-D-sorbitol 

Relevant articles and documents

Preparation of sugar-derived α-acetoxy-aldehydes

A convenient method for conversion of sugar diols (2a-2d) into a-acetoxy-aldehydes: 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranos-6-ulose (5a), 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranos-6-ulose (5b), methyl 6-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco- and L-glycero-α-D-gluco-heptopyranosid-7-uloses (5c and 5d respectively) is presented. This involves the protection (as TBDMS ether) of the primary hydroxyl group, acetylation of the remaining secondary one and desilylation followed by a Swern oxidation. Partial migration of the acetyl group during desilylation (with Bu4NF) was observed for compound 4a and complete migration for 4f. α-Acetoxy-aldehydes 5a-5d were characterized as adducts with Ph3P = CH-CO2Me (12a-12d).