66252-76-4

Basic information

• Product Name: 28-O-acetylbetulin 3-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranoside)
• Synonyms: 28-O-acetylbetulin 3-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranoside)
• CAS NO: 66252-76-4
• Molecular Weight: 815.055
• Mol File: 66252-76-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 28-O-acetylbetulin 3-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranoside)(CAS DataBase Reference)
• NIST Chemistry Reference: 28-O-acetylbetulin 3-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranoside)(66252-76-4)
• EPA Substance Registry System: 28-O-acetylbetulin 3-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranoside)(66252-76-4)

Safety Data

• Hazardous Substances Data: 66252-76-4(Hazardous Substances Data)

Upstream product

• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 473-98-3 betulin 
• 27686-35-7 28-acetoxybetulin 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Relevant articles and documents

GLYCOSYLATION OF TRITERPENE ALCOHOLS OF THE LUPANE SERIES

The glycosylation of lupeol, allobetulin, 3β-28-dihydroxy-18-lupene, 3β-28-dihydroxy-18β,19β-epoxylupane and of betulin monoacetates in acetonitrile with mercury cyanide has ben studied.The 3- and 28-mono- and the 3,28-di-O-β-D-glucopyranosides of 3β-28-dihydroxy-18-lupene and of 3β-28-dihydroxy-18β,19β-epoxylupane have been synthesized for the first time.Preparative methods for the synthesis of glucosides of lupeol, of allobetulin, and of betulin 3- and 28-monoacetates are proposed.

SYNTHESIS OF TRITERPENE AND STEROID GLYCOSIDES

The glycosylation of cholesterol, β-sitosterol, 28-O-acetylbetulin, and betulin with acylated glycosyl halides in the presence of Hg(OAc)2, Hg(CN)2, CdCO3, Ag2O, Ag2CO3, and HgO + HgBr2 usually gives acylated αβ-glycosides accompanied by acetates, ethers, and bromo and unsaturated derivatives of the initial alcohols.The use of Hg(CN)2 gave mainly β anomers (40-87percent), whereas α anomers preponderated when Hg(OAc)2 was the catalyst.When there was a deficiency of hydrogen halide acceptor and in the presence of the acidic catalyst HgBr2*HBr, the β anomer, produced initially, underwent anomerisation.Cholesteryl α-D-glucopyranoside tetra-acetate (48percent) was obtained by anomerisation of the β anomer.