title: Stereoselective synthesis of beta-phenylselenoglycosides from glycals and rationalization of the selenoglycosylation processes.
abstract: 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.
authors.affiliation: Dipartimento di Scienze Farmaceutiche, sede Chimica Biorganica e Biofarmacia, Università di Pisa,Via Bonanno 33, 56126 Pisa, Italy. valeriadb@farm.unipi.it
authors.forename: Valeria
authors.initials: V
authors.lastname: Di Bussolo
authors.forename: Annalisa
authors.initials: A
authors.lastname: Fiasella
authors.forename: Federica
authors.initials: F
authors.lastname: Balzano
authors.forename: Gloria
authors.initials: G
authors.lastname: Uccello Barretta
authors.forename: Paolo
authors.initials: P
authors.lastname: Crotti
mesh_terms: D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012643:Selenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D012643:Selenium