Synthesis of three 3-C-hydroxymethylpentoses with the D-ribo-, D-xylo- and L-lyxo-configurations. Identification of the latter with a monosaccharide isolated from phase I Coxiella burnetii lipopolysaccharide.

Abstract

Three 3-C-hydroxymethylpentoses with the D-ribo-, D-xylo and L-lyxo-configurations, were synthesised via nitromethane addition for the first two and 1,3-dithiane addition for the last one, to appropriate 3-ulose derivatives. 3-C-Hydroxy-methyl-L-lyxose is identical with a monosaccharide component previously isolated from hydrolysates of the phase I Coxiella burnetii lipopolysaccharide.