A NEW WAY FOR THE SYNTHESIS OF 3-AMINO SUGARS

Abstract

A preferential tendency to form six-membered rings exists when a dialdehyde produced by the action of 2 moles of sodium periodate on methyl-[beta]-L-arabinopyrano-side with nitromethane is condensed. In the pyranoside the original CHOH in position 3 is replaced by CHNO2, thus producing 3-nitro-3-deoxy-glycosides, a new class of sugar derivatives. The reaction yields the expected mixture of 3-nitro-pyranosides from which one isomer could be isolated as a crystalline sodium salt in about 40% yield. Upon catalytic hydrogenation of the free nitro compound, a crystalline methyl-3-amino-3-deoxy-pentoside (m.p. 189[degree], [[alpha]]D= + 63.5[degree], in water) was obtained. The free amino sugar hydrochloride was also prepared from the crystalline methyl-3-amino-3-deoxy-pentoside hydrochloride. The analogous series of reactions was also applied with success to a representative of the hexoses.