Studies on nitro sugars : Part II. Synthesis of benzyl 3,5- DI- O-benzyl-2-deoxy-2-Nitro-α- D-xylofuranoside and its transglycosylation with alkali

Abstract

Oxidation of benzyl 3,5-di- O-benzyl-2-oximino-α- D- threo-pentofuranoside ( 6) with trifluoroperoxyacetic acid afforded benzyl 3,5-di- O-benzyl-2-deoxy-2-nitro-α- D-xylofuranoside ( 8) in 83% yield. Transglycosylation of 8 to give the corresponding methyl xyloside ( 10) was achieved in alkaline methanol at room temperature, proceeding probably via an intermediate 2-nitroglycal ( 9). The structures of 8 and 10 were determined from their specific rotations and p.m.r. spectra.