Stereoselective synthesis of 2,3-unsaturated-aza-O-glycosides via new diastereoisomeric N-Cbz-imino glycal-derived allyl epoxides.
Diastereoisomeric D,L-N-Cbz-imino glycal-derived allyl epoxides 5 and 6 have been synthesized, and their addition reactions with alcohols examined. The reactions lead to the corresponding 2,3-unsaturated-aza-O-glycosides through a new, completely regioselective 1,4-addition process which proceeds with complete substrate-dependent stereoselectivity.
Di Bussolo
Valeria
V
Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, I-56126 Pisa, Italy.
Fiasella
Annalisa
A
Romano
Maria Rosaria
MR
Favero
Lucilla
L
Pineschi
Mauro
M
Crotti
Paolo
P