Stereoselective synthesis of beta-phenylselenoglycosides from glycals and rationalization of the selenoglycosylation processes.
Beta-phenylselenoglycosides have been efficiently and stereoselectively synthesized by direct oxidative glycosylation of benzenselenolate (PhSe(-)) with glycals. A rationalization of the presently described beta-selectivity and the opposite alpha-selectivity reported by Danishefsky in the ring-opening of epoxy glycals with benzeneselenol (PhSeH) is proposed.
Di Bussolo
Valeria
V
Dipartimento di Scienze Farmaceutiche, sede Chimica Biorganica e Biofarmacia, Università di Pisa,Via Bonanno 33, 56126 Pisa, Italy. valeriadb@farm.unipi.it
Fiasella
Annalisa
A
Balzano
Federica
F
Uccello Barretta
Gloria
G
Crotti
Paolo
P
D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012643:Selenium / Q000737:chemistry*; D013237:Stereoisomerism
D006027:Glycosides; D012643:Selenium