Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor.

Highlights: [•] The reactivity of both anomers of 6-O-protected allosamine and glucosamine acceptors with a superarmed donor was assessed. [•] Glucosamine derivatives react with the same selectivity as with disarmed donors, i.e. driven by electronic effects. [•] Allosamine derivatives react exclusively by the equatorial O-4, i.e. driven by steric factors. [Copyright &y& Elsevier]