Stereoselective synthesis of 2,3-unsaturated 1,6-oligosaccharides by means of a glycal-derived allyl epoxide and N-nosyl aziridine.
beta-D-threo- and 4-deoxy-4-amino-alpha-D-erythro-hex-2-enopyranosyl di- (n = 0) and trisaccharides (n = 1) of types A and B were synthetized by means of a reiterative, completely stereoselective glycosylation process which makes use of the D-galactal-derived allyl epoxide 1beta and D-allal-derived allyl N-nosyl aziridine 2alpha, respectively.
Di Bussolo
Valeria
V
Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Pisa, Italy.
Checchia
Lorenzo
L
Romano
Maria Rosaria
MR
Pineschi
Mauro
M
Crotti
Paolo
P
D001388:Aziridines / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001388:Aziridines; D004852:Epoxy Compounds; D009844:Oligosaccharides; C033132:aziridine