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Stereoselective Synthesis of β-Phenylselenoglycosides from Glycals and Rationalization of the Selenoglycosylation Processes

2010; American Chemical Society; Volume: 75; Issue: 12 Linguagem: Inglês

10.1021/jo100145s

1520-6904

Valeria Di Bussolo, Annalisa Fiasella, Federica Balzano, Gloria Uccello‐Barretta, Paolo Crotti,

Glycosylation and Glycoproteins Research

β-Phenylselenoglycosides have been efficiently and stereoselectively synthesized by direct oxidative glycosylation of benzenselenolate (PhSe−) with glycals. A rationalization of the presently described β-selectivity and the opposite α-selectivity reported by Danishefsky in the ring-opening of epoxy glycals with benzeneselenol (PhSeH) is proposed.