engleski

Theoretical study of acyl migrations on a carbohydrate ring

Although there are many experimental observations of acyl group migration on carbohydrate rings, 1, 2 none of the molecular modelling attempts of their mechanism clarification did not give convincing results.3, 4 The aim of this work is to explain the mechanism of O-2 to O-3 trans acyl migration on a model compound (methyl-2-O-acetyl-alfa-D-xylopyranoside) using high level quantum-chemical calculations. In solution there are several possible migration mechanisms, all of which presumably go through an ortho-acid, whose existence has been recently proved by the experiment.5 Gas phase mechanisms are different from those in the solution, and the individual solvent molecules have to be included in the calculations.

acyl migration; mechanisms; quantum-mechanical calculations

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