Synthesis of some 3-deoxy-D-ribofuranose derivatives

Abstract

Two routes to 3-deoxyribofuranose derivatives are described, the first via 3-deoxy-1,2-O-isopropylidene-D-glucofuranose and the second through the unsaturated aldehyde, 3-deoxy-1,2-O-isopropylidene-D-glycero-pentodialdo-1,4-furanos-3-ene. The latter on reduction to 3-deoxy-1,2-O-isopropylidene-L-threo-pentodialdo-1,4-furanose followed by a base-catalysed epimerisation at C(4) gives the corresponding D-erythro-isomer, from which 3-deoxy-1,2-O-isopropylidene-D-ribofuranose is obtained by borohydride reduction.