title: Stereoselective synthesis of 4-(N-mesylamino)-2,3-unsaturated- alpha-O-glycosides via a new glycal-derived vinyl alpha-N-(mesyl)-aziridine.
abstract: [reaction: see text] N-Mesyl aziridine 7alpha, a new activated vinyl aziridine derived from d-glucal, has been synthesized by cyclization of trans-N,O-dimesylate 6 with t-BuOK in anhydrous benzene. The reaction of 7alpha with alcohols, phenol, and monosaccharides (O-nucleophiles) leads to the corresponding 4-N-(mesylamino)-2,3-unsaturated-O-glycosides and disaccharides through a completely regioselective 1,4-addition process that proceeds with high or complete alpha-stereoselectivity.
authors.affiliation: Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, I-56126 Pisa, Italy.
authors.forename: Valeria
authors.initials: V
authors.lastname: Di Bussolo
authors.forename: Maria Rosaria
authors.initials: MR
authors.lastname: Romano
authors.forename: Mauro
authors.initials: M
authors.lastname: Pineschi
authors.forename: Paolo
authors.initials: P
authors.lastname: Crotti
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D003500:Cyclization; D006027:Glycosides / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D006027:Glycosides; C033132:aziridine