[GRAPHICS] Epoxide 4 is generated in situ from D-glucal-derived hydroxy mesylate 3. Reaction of epoxide 4 with a series of alkyl- and aryllithium reagents affords 2,3-unsaturated beta-C-glycosides with excellent 1,4-regioselectivity and complete stereoselectivity for the beta-glycoside. Other organometallic reagents demonstrate more complex behavior in their reactions with epoxide 4.

New Stereoselective beta-C-glycosidation by Uncatalized 1,4-Addition of Organolithium Reagents to a Glycal-derived Vinyl Oxirane

DI BUSSOLO, VALERIA;PINESCHI, MAURO;CROTTI, PAOLO
2003

Abstract

[GRAPHICS] Epoxide 4 is generated in situ from D-glucal-derived hydroxy mesylate 3. Reaction of epoxide 4 with a series of alkyl- and aryllithium reagents affords 2,3-unsaturated beta-C-glycosides with excellent 1,4-regioselectivity and complete stereoselectivity for the beta-glycoside. Other organometallic reagents demonstrate more complex behavior in their reactions with epoxide 4.
DI BUSSOLO, Valeria; M., Caselli; Pineschi, Mauro; Crotti, Paolo
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/205932
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