FormylC-Glycosides as Precursors to Glycosyl Nitrile Oxides and Nitrones

Formyl C-glycosides, prepared via the thiazole-based formylation of sugar lactones in three steps, are readily condensed with N-benzylhydroxylamine and hydroxylamine to give the corresponding glycosyl nitrones and oximes respectively. The latter imino derivatives are the precursors to nitrile oxides via the N-bromosuccinimide method.