Studies in Sugar Chemistry. 2. A Simple Method for O-Deacylation of Polyacylated Sugars

Article abstract of DOI:10.1021/jo00355a026

Total solvolytic O-deacylation of polyacylated sugars is readily accomplished upon stirring for 15 min - 6 h a solution of a sugar in methanol in the presence of catalytic amount of cyanide.The reaction proceeds in high yields, under neutral conditions, at room temperature.The overall rate of the reaction, readily followed by observing the changes in the 1H 300-MHz NMR spectra, is greatly influenced by the substituent at the anomeric position in the order of 1-OH > 1-OAc >> 1-OR.