Regioselective glycosylation reactions based on computational predictions

Regioselectivity is a major issue in glycosylation reactions. Better understanding of regioselectivity of acceptors can greatly facilitate and simplify the syntheses of oligosaccharides. The reactivity of diol acceptors is often affected by stereochemistry and protecting groups, which make prediction the regioselectivity of diol acceptors extremely difficult. Quantum mechanic methods were used to study the relationship between protecting groups and reactivity of diol acceptor and a correlation between Fukui function and regioselectivity is established through series of glycosylation reactions.