On The Conversion of Arabino- and Ribofuranosyl Methyl Glycosides to Their 1-O-Acetyl Derivatives

Abstract Improved conditions for the acetolysis of methyl 2,3,5-tri-O-benzyl-α-and β-L-arabinofuranosides and 2,3,5-tri-O-benzoyl-α-and β-L-ribofuranosides have been investigated. In the case of the arabinofuranosides, reproducible acetolysis conditions were obtained by substantially decreasing the amount of sulphuric acid with respect to acetic acid-acetic anhydride mixtures. With the ribofuranosides low temperature acetolysis for a short time resulted in good isolated yield of the β-1-O-acetyl anomer.