A New and Convenient Synthesis of 1-O-Acetyl-2, 3, 5-tri-O-benzoyl-β-D-ribofuranose from Guanosine ; Some Observations on Solvolysis of 2', 3', 5'-Tri-O-benzoylguanosine

Abstract

Acetolysis of 2', 3', 5'-tri-O-benzoylguanosine with glacial acetic acid, acetic anhydride, and sulfuric acid gave rise to 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-D-ribofuranose in a fairly good yield (overall yield from guanosine was 50%). This method will afford a most convenient procedure for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-D-ribofuranose which is a key intermediate in the synthesis of ribonucleosides and ribonucleotides. The direct acetolysis is one of the rare cases in which N-glycosides are easily acetolyzed without cleavage of the furanoside ring. Some observations on hydrolysis and acetolysis of 2', 3', 5'-tri-O-benzoylguanosine were also described.