Stereoselective syntheses of 2,4:5,6-di-O-isopropylidene-1 -C-phenyl-<scp>D</scp>-glycero-<scp>D</scp>-ido-hexitol and 2,4:5,6-di-O-isopropylidene-1 -C-phenyl-<scp>D</scp>-glycero-<scp>D</scp>-gulo-hexitol from<scp>D</scp>-glycero-<scp>D</scp>-gulo-heptono-γ-lactone. X-Ray structure of 1 -O-acetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-<scp>D</scp>-glycero-<scp>D</scp>-ido-hexitol

Abstract

D-glycero-D-gulo-Heptonolactone has been converted by three consecutive reactions (acetonation, reduction and glycol cleavage reaction) into 2,4:5,6-di-O-isopropylidene-D-glucose which with phenylmagnesium bromide gave preponderantly 2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol 5. 2,4:5,6-Di-O-isopropylidene-1-C-phenyl-D-glycero-D-gulo-hexitol 6 has been obtained from 5via an oxidation–reduction sequence. The structure of 5 has been confirmed by X-ray crystallographic analysis of its 1 -O-acetyl-derivative 12.