Synthesis and X-ray studies of novel 3-C-nitromethyl-hexofuranoses

Abstract

A practical method for the synthesis of three novel 3-C-nitromethyl-hexofuranoses is reported. The Henry reaction on a 1,2:5,6-di-O-isopropylidene-α-d-gulofuranose-derived ketone provided a 3-C-branched gulo-isomer as the sole reaction product. The dehydration-rehydration of the latter yielded an isopropylidene-protected 3-C-nitromethyl-galactofuranose. The reaction sequence can be also used for the synthesis of a 3-deoxy-3-C-nitromethyl-hexofuranose derivative with a gulo-configuration. Two of the newly obtained carbohydrate derivatives were characterized by X-ray crystallography.

Keywords: 3-C-Nitromethyl-galactofuranose; 3-C-Nitromethyl-gulofuranose; Altona–Sundaralingam pseudorotation phase angle; Conformations; Henry reaction.