Synthesis, Configurational and Conformational Studies of Six Amino Sugar Precursors Formed by [3+2]Cycloaddition of Alkylnitrile Oxides to Enone Sugars

An easy and efficient synthesis of a novel bicyclic system (isoxazolino-pyranoside), obtained by the 1,3-dipolar cycloaddition of acetonitrile and propionitrile oxides to highly reactive α,β-unsaturated sugar enones, is described. The configuration and conformation of these new compounds were inferred from their spectroscopic data.