New stereoselective beta-glycosylation via a vinyl oxirane derived from D-glucal.
[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.
Bussolo
Valeria Di
VD
Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, I-56126 Pisa, Italy.
Caselli
Micaela
M
Pineschi
Mauro
M
Crotti
Paolo
P
D002125:Calcium Gluconate / Q000737:chemistry*; D005027:Ethylene Oxide / Q000737:chemistry*; D006031:Glycosylation; D013237:Stereoisomerism
D005027:Ethylene Oxide; D002125:Calcium Gluconate