Stereoselective Dihydroxylation Reaction of Alkenyl ß-D-Hexopyranosides: A Methodology for the Synthesis of Glycosylglycerol Derivatives and 1-O-Acyl-3-O-ß-D-glycosyl-sn-glycerol Analogues

A variety of new glycosylglycerol derivatives have been prepared by stereoselective dihydroxylation of a range of alkenyl beta-D-hexopyanosides under Donohoe's conditions. We have studied the relationship between the diastereoisomeric excess and the structural features of the precursor (sugar and alkenyl moieties). The stereochemical yields demonstrated that the presence of a hydrogen-bond donor group (OH, NHAc) at the 2-position of the sugar moiety is required to obtain high levels of stereofacial discrimination. New 1-O-acyl-3-O-beta-D-glycosyl-sn-glycerol analogues were obtained by functionalisation of the primary hydroxy group with a fatty acid. Preliminary cytotoxic activity assays of both glycosylglycerol and glycoglycerolipid analogues are also presented.