Studies in Sugar Chemistry. 2.1A Simple Method for O-Deacylation of Polyacylated Sugars

Jacob Herzig, Abraham Nudelman, Hugo E. Gottlieb, Bilha Fischer

Research output: Contribution to journalArticlepeer-review

118 Scopus citations

Abstract

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 a 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.

Original languageEnglish
Pages (from-to)727-730
Number of pages4
JournalJournal of Organic Chemistry
Volume51
Issue number5
DOIs
StatePublished - 1986

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