A Simple Synthesis of 8-(Methoxycarbonyl)octyl 3,6-Di-O-(α-D-mannopyranosyl)-α-D-mannopyranoside and Derivatives and Their Use in the Preparation of Neoglycoconjugates.

Abstract 8-(Methoxycarbonyl)octyl 3,6-di- O -(α- d -mannopyranosyl)-α- d -mannopyranoside ( 10 ) was synthesized in 54% yield by regioselective diglycosylation of unprotected mannoside 4 , employing the trichloroacetimidate donor 1 , followed by debenzoylation. Derivatives of compounds 4 and 10 were used to prepare conjugates containing fluorochromes for the study of carbohydrate–lectin interactions, as well as conjugates with phospholipids for the preparation of liposomes.