Thio-glycomimetics with enhanced lipophilicity and their biological activity

The thio-linked glycomimetics were prepared via a base-catalyzed, highly stereo-selective Michael condensation of levoglucosenone with various sugar, heterocyclic and adamantane thiols in order to generate a library of analogs with comparative level of lipophilicity for further biological screening as antibacterial and anticancer agents. The comparative analysis of earlier synthesized library of previously synthesized glycomimetics with the new analogs exhibiting more lipophilic character is also presented. H-1 NMR, C-13 NMR, and single-crystal x-ray diffraction of the unexpected addition and cyclization product unequivocally confirm the structural assignments. Mechanistic insights related to the synthesis of new products are also proposed and discussed.