Stereoselective synthesis of 4-(N-mesylamino)-2,3-unsaturated- alpha-O-glycosides via a new glycal-derived vinyl alpha-N-(mesyl)-aziridine.
[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.
Di Bussolo
Valeria
V
Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, I-56126 Pisa, Italy.
Romano
Maria Rosaria
MR
Pineschi
Mauro
M
Crotti
Paolo
P
D001388:Aziridines / Q000737:chemistry*; D003500:Cyclization; D006027:Glycosides / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
D001388:Aziridines; D006027:Glycosides; C033132:aziridine