Reduction of glycosylnitromethanes to glycosylmethylamines with ferrous salts

Abstract

Reduction of β-D-galactopyranosylnitromethane, β-D-glucopyranosylnitromethane and 1-deoxy-1-nitro-D-glycero-L-manno-heptitol with ferrous hydroxide afforded β-D-galactopyranosylmethylamine (I), β-D-glucopyranosylmethylamine (II) and 1-amino-1-deoxy-D-glycero-L-manno-heptitol (III), respectively. Thanks to the high conversion of the nitro derivatives and the simple isolation, this method is very suitable for preparation of glycosylmethylamines. The structure of products in their underivatized form was proved by mass spectrometry.