84094-19-9

Basic information

• Product Name: methyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-allopyranosyl)-β-D-allopyranoside
• Synonyms: methyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-allopyranosyl)-β-D-allopyranoside
• CAS NO: 84094-19-9
• Molecular Weight: 654.622
• Mol File: 84094-19-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-allopyranosyl)-β-D-allopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-allopyranosyl)-β-D-allopyranoside(84094-19-9)
• EPA Substance Registry System: methyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-allopyranosyl)-β-D-allopyranoside(84094-19-9)

Safety Data

• Hazardous Substances Data: 84094-19-9(Hazardous Substances Data)

Upstream product

• 7216-73-1 methyl β-D-cellobioside 
• 74895-01-5 methyl 4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-β-D-glucopyranoside 
• 84094-16-6 methyl 4-O-<4,6-O-benzylidene-2,3-di-O-(methylsulfonyl)-β-D-glucopyranosyl>-2,3,6-tri-O-(methylsulfonyl)-β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 108-24-7 acetic anhydride 
• 84094-18-8 methyl 2,6-di-O-benzoyl-4-O-<3-O-benzoyl-4,6-O-benzylidene-2-O-(methylsulfonyl)-β-D-allopyranosyl>-2-O-(methylsulfonyl)-β-D-allopyranoside 
• 7216-69-5 methyl β-D-lactopyranoside 
• 137119-40-5 methyl 4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 

Downstream Products

• 129905-23-3 methyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 84094-20-2 methyl 4-O-(4,6-O-benzylidene-β-D-allopyranosyl)-β-D-allopyranoside 

Relevant articles and documents

FeCl3 mediated arylidenation of carbohydrates

Glycosides and thioglycosides based on monosaccharides in reaction with benzaldehyde dimethylacetal or p-methoxybenzaldehyde dimethyl acetal undergo FeCl3-catalyzed (20 mol %) regioselective 4,6-O-arylidenation producing the corresponding acetals in high yields. FeCl3 also mediates acetalation of glycosides and thioglycosides of cellobiose, maltose, and lactose affording the corresponding 4′,6′-O-benzylidene acetals, which were isolated after their acetylation in situ with acetic anhydride and pyridine. The combined yields (two steps) of these final products are also high (61-84%). The procedure is applicable to a wide variety of functional groups including -OBn.

CHEMICAL MODIFICATION OF METHYL β-CELLOBIOSIDE

Treatment of methyl β-cellobioside (1) with α,α-dimethoxytoluene in N,N-dimethylformamide in the presence of p-toluenesulfonic acid gave a high yield of methyl 4',6'-O-benzylidene-β-cellobioside (6), which was transformed into methyl 2,3,2',3',4',6'-hexa-