1187445-23-3

Basic information

• Product Name: methyl 2-O-acetyl-3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
• Synonyms: methyl 2-O-acetyl-3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
• CAS NO: 1187445-23-3
• Molecular Weight: 690.831
• Mol File: 1187445-23-3.mol

Chemical Properties

• CAS DataBase Reference: methyl 2-O-acetyl-3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-O-acetyl-3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside(1187445-23-3)
• EPA Substance Registry System: methyl 2-O-acetyl-3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside(1187445-23-3)

Safety Data

• Hazardous Substances Data: 1187445-23-3(Hazardous Substances Data)

Upstream product

• 35958-64-6 3,5,6-Tri-O-benzyl-D-glucofuranose 
• 1005004-09-0 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranose 
• 1005004-07-8 1,2-di-O-acetyl-3,5,6-tri-O-benzyl-4a-carba-β-D-xylohex-4(4a)-enofuranose 
• 1005004-04-5 (2S,4S,5S,6R)-1,2,4-tri-O-benzyl-3-methyleneoct-7-ene-1,2,4,5,6-pentaol 
• 1187445-13-1 methyl 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 108-24-7 acetic anhydride 
• 1187444-83-2 1,2-anhydro-3,5,6-tri-O-benzyl-4a-carba-α-D-galactofuranose 

Relevant articles and documents

Carbasugar analogues of galactofuranosides: β-O-linked derivatives and towards β-S-linked derivatives

A selectively protected carbasugar analogue of β-galactofuranose was synthesised from glucose using ring-closing metathesis as the key step. The carbasugar was converted into an α-galacto configured 1,2-epoxide, which was an effective electrophile in Lewis acid catalysed coupling reactions with alcohols. The epoxide was opened with regioselective attack at C-1 to give β-galacto configured C-1 ethers. Using carbohydrates as nucleophiles, we synthesised a number of pseudodisaccharides. The epoxide was also regioselectively opened at C-1 with a sulfur nucleophile under basic conditions to give a β-galacto configured C-1 thioether.

Synthesis of carbadisaccharide mimics of galactofuranosides

A partially protected carbagalactofuranose was converted into a 1,2-anhydro derivative. This epoxide was opened with alcohol nucleophiles under Lewis acid catalysis to give β-carbagalactofuranose pseudodisaccharides with excellent regioselectivity.