Stereochemistry of Nucleophilic Addition Reactions. VIII. Preparation of 1,5-Anhydro-4,6-<i>O</i>-benzylidene-2,3-dideoxy-3-nitro-<scp>d</scp>-<i>erytho</i>-hex-2-enitol and Its Reactions with Some Nucleophiles

Abstract

Abstract The title compound was synthesized from 1,5-anhydro-d-glucitol via nitromethane cyclization. The reduction of the compound with sodium borodeuteride afforded a mixture of saturated nitro compounds having an axial and equatorial deuterium atom at C-2 in an approximate ratio of 2:1. On the other hand, the reaction with hydrogen cyanide gave predominantly the adduct with the manno configuration, together with small amounts of a cyano olefin. The reaction with hydrazoic acid yielded addition products with the gluco and manno configurations; the ratio was strongly affected by the solvent used.