Abstract
The synthesis of 7-deoxy-D-glycero-D-gluco-heptose (1) from 3, 5-O-benzylidene-1, 2-O-isopropylidene-α-D-glucofuranose (2) is described. Oxidation of compound (2) afforded 3, 5-O-benzylidene-1, 2-O-isopropylidene-α-D-gluco-hexodialdo-1, 4-furanose (3), which was then treated with methylmagnesium iodide to give 3, 5-O-benzylidene-1, 2-O-isopropylidene-7-deoxy-α-D-glycero-D-gluco-heptose (4) and its L-glycero-D-gluco isomer (5). Hydrolysis of (4) produced compound (1), which was identical with natural SF-666 A, a fermentation product of Streptomyces setonensis nov. sp.
