POSSIBLE MODEL FOR A NEW CHIRAL GLYCERIDE SYNTHESIS .1. SYNTHESIS OF 1-O-AROYL-2-O-TOSYL-SN-GLYCEROLS

A procedure has been developed which permits the synthesis of mixed-acid 1,2-di-O-aroyl-sn-glycerols via 1,6-di-O-aroyl-2,5-di-O-tosyl-D-mannitol. The method was applied to the synthesis of some (S)-(+)-1-O-aroyl-2-O-tosyl-sn- glycerols. In order to check the structure and the optical purity of the 1,2-diglycerides, tritylation to give 3-trityl ethers was carried out. 1-Trityl ethers were prepared by a second method via 3-O-aroyl-sn-glycerols. The optical rotations of the 3- and 1-trityl ethers were compared. Oxidation of 1,6-di-O-aroyl-2,5-di-O-tosyl-D-mannitol at temperatures above 25 °C took place with complete or partial racemisation.