Stereoselective reaction of methyl α- and β-D-glycopyranosides with acetic anhydride in the presence of trimethylsilyl trifluoromethanesulphonate
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 1490-1492
- https://doi.org/10.1039/p19900001490
Abstract
Treatment of methyl β-D-glycopyranosides with TMSOtf–Ac2O gives acyclic products by selective cleavage of the ring carbon–oxygen bond, whereas methyl α-D-isomers undergo replacement of the anomeric methoxy by an acetoxy group with retention of configuration.This publication has 2 references indexed in Scilit:
- A new method for cleaving methyl and methylthiomethyl ethersTetrahedron Letters, 1983
- Derivatives of the Aldehydrol Form of Sugars. III.1 Carbon One AsymmetryJournal of the American Chemical Society, 1940