The Synthesis of Nitro and Dimeric Nitroso Sugars by Peracid Oxidation of Amino Sugars

Abstract

A number of methyl 3-amino-3-deoxyaldopyranosides were oxidized with m-chloroperbenzoic acid. The reaction, which had been previously applied to steroidal amines (6), has provided a new route to nitro sugars and at the same time furnished hitherto unknown nitroso sugar derivatives, namely, dimeric methyl 3-deoxy-3-nitrosoaldopyranosides. Oxidation of a model compound, trans-2-aminocyclohexanol, likewise gave the corresponding nitro and dimeric nitroso alcohols. The combined yields of oxidation products ranged from 40 to 95%.