Practical synthesis of N-alkyl-N-glycosylhydroxylamines, multitalented precursors of enantiomerically pure nitrones

A practical synthesis of N-benzyl-N-glycosylhydroxylamines 3 (R=CH2Ph) is reported. The ability of these compounds to act as versatile synthetic intermediates is demonstrated by their oxidation followed by cycloaddition to N-glycosyl isoxazolidines and by the novel direct cycloaddition as masked acyclic, highly functionalized chiral nitrones.