Synthesis and Optical Resolution of 4, 6-Dideoxy-3, 5-O-isopropylidene-2-O-(methoxymethyl)-DL-glucitol

Abstract

4, 6-Dideoxy-3, 5-O-isopropylidene-2-O-(methoxymethyl)-DL-glucitol (3) was conveniently prepared from (±)-parasorbic acid (4). Resolution of the racemate 3 into the D-and L-isomers, each of which serves as a synthetic building block for the sugar moiety of naturally occurring (-)-griseusin A (2) or its enantiomer (1), was effected by high-performance liquid chromatography of its benzoate (12) on a column packed with (+)-poly (triphenylmethylmethacrylate) on macroporous silica gel [Chiralpak OT (+)^[O!R]].