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

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

doi:10.1021/jo00355a026

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

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

Department of Chemistry

Teva Pharmaceutical Industries Ltd.

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119 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 language	English
Pages (from-to)	727-730
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	51
Issue number	5
DOIs	https://doi.org/10.1021/jo00355a026
State	Published - 1986

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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.",

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AB - 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.

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

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