1385089-80-4

Basic information

• Product Name: methyl 2,3-di-O-benzyl-β-D-idopyranoside
• Synonyms: methyl 2,3-di-O-benzyl-β-D-idopyranoside
• CAS NO: 1385089-80-4
• Molecular Weight: 374.434
• Mol File: 1385089-80-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl 2,3-di-O-benzyl-β-D-idopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3-di-O-benzyl-β-D-idopyranoside(1385089-80-4)
• EPA Substance Registry System: methyl 2,3-di-O-benzyl-β-D-idopyranoside(1385089-80-4)

Safety Data

• Hazardous Substances Data: 1385089-80-4(Hazardous Substances Data)

Upstream product

• 1824-94-8 methyl beta-D-galactopyranoside 
• 1385089-67-7 methyl 3-O-benzyl-4,6-O-benzylidene-β-D-idopyranoside 
• 100-39-0 benzyl bromide 
• 1385089-78-0 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-idopyranoside 
• 6748-86-3 methyl 4,6-O-benzylidene-β-D-galactopyranoside 2,3-di-O-p-toluenesulfonate 

Downstream Products

• 128184-63-4 methyl 2,3,4-tri-O-benzyl-β-D-idopyranoside 
• 128184-64-5 methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-β-D-ido-hept-6-enopyranoside 
• 138875-24-8 methyl 2,3,4-tri-O-benzyl-b-D-ido-hexodialdo-1,5-pyranoside 
• 166592-73-0 methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-β-D-idopyranoside 

Relevant articles and documents

Studies on the 6-homologation of β-D-idopyranosides

β-D-Idopyranosides are interesting sugars because of their unusual conformational flexibility in the pyranosyl ring, and also their β-1,2-cis-anomeric configuration. Here we report our studies of the regioselective opening of 4,6-O-benzylidene-protected β-D-idopyranosides under reducing conditions, and the subsequent 6-homologation via Swern oxidation and Wittig olefination to afford a 6,7-dideoxy-β-D-ido-hept-6-enopyranoside. This olefination product was found to adopt predominantly 1C4 conformation in solution by NMR experiments, which places the vinyl group at a more sterically hindered axial position and creates difficulty in subsequent hydroborations.