1173695-22-1

Basic information

• Product Name: 1-O-acetyl-2,3,5-tri-O-benzoyl-α-L-ribofuranose
• Synonyms: 1-O-acetyl-2,3,5-tri-O-benzoyl-α-L-ribofuranose
• CAS NO: 1173695-22-1
• Molecular Weight: 504.493
• Mol File: 1173695-22-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-O-acetyl-2,3,5-tri-O-benzoyl-α-L-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-acetyl-2,3,5-tri-O-benzoyl-α-L-ribofuranose(1173695-22-1)
• EPA Substance Registry System: 1-O-acetyl-2,3,5-tri-O-benzoyl-α-L-ribofuranose(1173695-22-1)

Safety Data

• Hazardous Substances Data: 1173695-22-1(Hazardous Substances Data)

Upstream product

• 3080-30-6 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose 
• 171866-28-7 1-O-methyl-2,3,5-tri-O-benzoyl-L-ribofuranose 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 

Downstream Products

• 3080-30-6 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose 
• 173009-65-9 1,2-di-O-acetyl-3,5-di-O-benzoyl-α-L-ribofuranose 
• 173009-66-0 1,2-di-O-acetyl-3,5-di-O-benzoyl-β-L-ribofuranose 
• 171721-03-2 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-L-arabinofuranosyl)thymine 
• 171866-29-8 1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose 
• 163252-36-6 clevudine 

Relevant articles and documents

Reaction kinetics and mechanism of sulfuric acid-catalyzed acetolysis of acylated methyl l-ribofuranosides

The mechanism of the sulfuric acid-catalyzed acetolysis of methyl 2,3,5-tri-O-acetyl- and methyl 2,3,5-tri-O-benzoyl-Lribofuranosides and the accompanying anomerization of both the starting material and the 1,2,3,5-tetra-O-acetyl- and 1-O-acetyl-2,3,5-tri-O-benzoyl-L-ribofuranoses formed was investigated. The progress of the reactions was followed by 1H NMR spectroscopy and the rate constants for the reactions were determined for a proposed kinetic model. The role of H+ and Ac + as the catalytically active species was clarified, proving that the anomerization of the acylated methyl furanosides is activated by protonation, while, on the contrary, the anomerization of the 1-O-acetyl ribofuranoses is activated by the acetyl cation. The anomerization of the acylated methyl furanosides was verified to be activated on the ring oxygen leading to endocyclic CO-bond rupture while the 1O-acetyl ribofuranoses are activated on the acetyloxy group on C(1) leading to exocyclic cleavage.

METHOD FOR PRODUCTION OF FURANOSE DERIVATIVE

An object of the present invention is to provide a industrially appropriate method for producing the β-anomers of ribofuranose derivatives in a highly selective manner at a high yield. The present invention provides a method for producing ribofuranose derivatives wherein β-anomers is precipitated from among the generated furanose derivatives by controlling the amount of a reaction reagent used and/or using a poor solvent in the acetolysis reactions of 2,3,5-tri-O-acyl-1-O-alkyl-ribofuranose and 2,3-di-O-acyl-1-O-alkyl-5-deoxy-ribofuranose.