Action of Strong Acids on Acetylated Glycosides. XIII. Studies on the Mechanism of the Anomerisation Reaction.

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Abstract
The anomerisation of some acetylated glycosides in sulphuric acid-acetic anhydride- acetic acid has been studied. Replacement of the 2-O-acetyl group of isopropyl-tetra-O-acetyl-[beta]-D-glucopyranoside with a methyl group results in a higher rate of reaction. Thus participation of the 2-O-acetyl group does not seem to facilitate the reaction. For a 2-deoxy-glucopyranoside and a galactofuranoside the acetolysis was so fast that no anomerisation could be observed.

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