Synthesis of Isosteric Analogs of Acylglycosylglycerols Active as Chemoprevention Agents

Monoacylated glycosylglycerols are known anti-tumor promoters: in order to study the role of the ester function in the modulation of their activity, we synthesized several analogues in which the acyloxy moiety was substituted with isosteric chains linked to the glycosylglycerol skeleton through an ether or a ketone functionality or simply by a C-C bond. Depending on the position of the chain, the key steps in the synthesis were either the coupling of suitable chiral synthons with the sugar, with complete stereocontrol over the anomeric configuration, or regioselective elaboration at position 6 of the sugar.