An efficient stereoselective synthesis of enantiomerically pure mono- and di-O-hexadecyl-beta-D-glucosylglycerol ethers by epoxidation of an allyl-beta-D-glucopyranoside asymmetrically induced by the glucide moiety

1-O-Hexadecyl and 1,2-di-O-hexadecyl-3-O-(beta-D-glucopyranosyl)-sn-glycerol ethers were obtained by regiospecific opening of the oxirane ring of the 2',3'-epoxypropyl 2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-glucopyranoside synthetized by stereoselective epoxidation of the corresponding allyl 3,4,6-tri-O-benzyl-beta-D-glucopyranoside asymmetrically induced by the glucide moiety. (C) 1997 Published by Elsevier Science Ltd