Syothesis of 3-Deoxy-3-nitro-D-xylose

Abstract

Crystalline 3-deoxy-3-nitro-α-D-xylose (5) was obtained in 40% over-all yield by periodate oxidation of 3-deoxy-1,2-O-isopropylidene-3-nitro-α-D-glucofuranose (2) followed by borohydride reduction and acid hydrolysis. In addition to the intermediate 3-deoxy-1,2-O-isopropylidene-3-nitro-α-D-xylofuranose (4), a small amount of an isomer probably having the D-ribo configuration was isolated. The title compound (5) was also obtained by hydrolysis of its methyl β-pyranoside (1).