Synthesis of α- and β-C-glycosides of N-acetylglucosamine

As part of efforts to make available new classes of bioactive C-glycoconjugates, d-glucosamine has been effectively converted into a series of 2-deoxy-2-amino-C-glycosides. This versatile approach is keyed by a remarkably effective metal catalyzed olefin isomerization of the isomeric C-allyl amino sugars which, in turn, are readily available via radical allylation of d-glucosamine.