Stereoselective synthesis of 2-O-MEM-2,3-unsaturated-β-O-glycosides and elaboration to useful synthetic tools

The glycosylation of alcohols by the new 2-O-MEM-substituted d-galactal-derived allyl epoxide affords the corresponding alkyl 2-O-MEM-3-deoxy-β-d-threo-hex-2-enopyranosides through a completely 1,4-regio- and a highly to completely substrate-dependent stereoselective glycosylation processes. The glycosides obtained can be regioselectively transformed into corresponding 3-deoxy-β-O-glycosides, 3-deoxy-β-d-threo-hexopyranosid-2-uloses, and 3,4-dideoxy-β-d-glycero-hex-3-enopyranosid-2-uloses, which are useful synthetic tools for further transformations.