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.
Stereoselective synthesis of 2-O-MEM-2,3-unsaturated-beta-O-glycosides and elaboration to useful synthetic tools
DI BUSSOLO, VALERIA;FAVERO, LUCILLA;CROTTI, PAOLO
2010-01-01
Abstract
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.File in questo prodotto:
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