Stereoselective synthesis of 4-amino-2,3-unsaturated-N-Cbz-imino-O-glycosides via new diastereoisomeric N-Cbz-imino glycal-derived allyl N-nosyl aziridines.
The glycosylation of alcohols by the new diastereoisomeric d,l-6-deoxy-N-Cbz-imino glycal-derived allyl N-nosyl aziridines 5 and 6 affords, after deprotection of the 4-(N-nosylamino) group, the corresponding 2,3-unsaturated-N-Cbz-imino-O-glycosides bearing a free amino group on C(4) through a completely 1,4-regio- and substrate-dependent stereoselective glycosylation process.
Di Bussolo
Valeria
V
Dipartimento di Scienze Farmaceutiche, sede Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, I-56126 Pisa, Italy. valeriadb@farm.unipi.it
Fiasella
Annalisa
A
Favero
Lucilla
L
Bertolini
Ferruccio
F
Crotti
Paolo
P
D000438:Alcohols / Q000737:chemistry; D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D050111:Imino Sugars / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D000617:Aminoglycosides; D001388:Aziridines; D006027:Glycosides; D050111:Imino Sugars