Stereoselective uncatalyzed synthesis of 2,3-unsaturated-4-n-substituted-beta-O-glycosides by means of a new D-galactal-derived N-(mesyl)-aziridine.
The reaction of the new D-galactal-derived allylic aziridine 1beta with O-nucleophiles (alcohols and monosaccharides) affords, in a high to complete beta-stereoselectivity, the corresponding 2,3-unsaturated-beta-O-glycosides bearing a beta-N-functionality at C4.
Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy.
Valeria
V
Di Bussolo
Maria Rosaria
MR
Romano
Lucilla
L
Favero
Mauro
M
Pineschi
Paolo
P
Crotti
D000438:Alcohols / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D005690:Galactose / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis*; D009005:Monosaccharides / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D001388:Aziridines; D006027:Glycosides; D009005:Monosaccharides; C033132:aziridine; D005690:Galactose