Computational study of the influence of cyclic protecting groups in stereoselectivity of glycosylation reactions.

Protecting groups often have profound influences on the stereoselectivity of glycosylation reactions. The effects of many protecting groups, especially cyclic protecting groups, are not well understood and difficult to explain and predict. Computational methods were used to study the effect of benzylidene acetal and cyclic carbonate protecting groups in glycosylation reactions, and the results provided a theoretical explanation for experimental observations.