title: New stereoselective beta-glycosylation via a vinyl oxirane derived from D-glucal.
abstract: [reaction: see text] The reaction of the vinyl oxirane 1 derived from D-glucal with a series of O-nucleophiles (alcohols, phenol, and diacetone D-glucose) affords the corresponding 2-unsaturated beta-O-glycosides in a completely stereoselective way (syn 1,4-addition pathway). Epoxide 1 is generated in situ by treatment of the corresponding hydroxy mesylate 2 with t-BuOK in anhydrous benzene.
authors.affiliation: Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, I-56126 Pisa, Italy.
authors.forename: Valeria Di
authors.initials: VD
authors.lastname: Bussolo
authors.forename: Micaela
authors.initials: M
authors.lastname: Caselli
authors.forename: Mauro
authors.initials: M
authors.lastname: Pineschi
authors.forename: Paolo
authors.initials: P
authors.lastname: Crotti
mesh_terms: D002125:Calcium Gluconate / Q000737:chemistry*; D005027:Ethylene Oxide / Q000737:chemistry*; D006031:Glycosylation; D013237:Stereoisomerism
chemical_list: D005027:Ethylene Oxide; D002125:Calcium Gluconate