Stereospecific uncatalyzed alpha-O-glycosylation and alpha-C-glycosidation by means of a new D-Gulal-derived alpha vinyl oxirane.
The reaction of alpha vinyl oxirane 5, prepared through a new route to the d-gulal system, with O-nucleophiles (alcohols and di-O-isopropylidene-alpha-d-monosaccharides) and C-nucleophiles (lithium alkyls) affords, in a completely stereoselective way, the corresponding 2-unsaturated alpha O- and C-glycosides having the same configuration as the starting epoxide.
Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy.
Valeria
V
Di Bussolo
Micaela
M
Caselli
Maria Rosaria
MR
Romano
Mauro
M
Pineschi
Paolo
P
Crotti
D004852:Epoxy Compounds / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D008968:Molecular Conformation; D013237:Stereoisomerism
D004852:Epoxy Compounds; D006027:Glycosides; C024370:3,4-epoxy-1-butene