Inositol Derivatives. V. Selective Benzoylation of 1,2-<i>O</i>-Cyclohexylidene-<i>myo</i>-inositol and Preparation of New <i>O</i>-<i>p</i>-Tolylsulfonyl-<i>myo</i>-inositols

Abstract

Abstract The reaction of l,2-O-cyclohexylidene-myo-inositol (1a) with 1.5 equiv. of benzoyl chloride below 0°C gave 3-O-benzoate (2a) predominantly in 40% yield, together with easily separable 3,6-di-O-benzoate (3a) in 2.5% yield. Selective sulfonylation of 2a gave three new O-p-tolylsulfonyl-myo-inositols (the 4,6- (8a), 4,5- (9a), and 4,5,6-p-toluenesulfonates (10)). From 3a, two O-p-tolylsulfonyl derivatives (5- (15a) and 4,5-p-toluenesulfonates (16)) were obtained. The relative reactivities, toward benzoylation, of the hydroxyl groups of 1a were shown to be almost similar to those observed in tosylation. The p-tolylsulfonyloxy function on C–5 of 10 was found to be readily displaced preferentially by chloride ion.