A novel strategy for oligosaccharide synthesis via temporarily deactivated S-thiazolyl glycosides as glycosyl acceptors.
A new glycosylation strategy that allows chemoselective activation of the S-thiazolyl (STaz) moiety of a glycosyl donor over the temporarily deactivated glycosyl acceptor, bearing the same anomeric group, has been developed. This deactivation is achieved by engaging of the STaz moiety of the glycosyl acceptor into a stable palladium(II) complex. Therefore, obtained disaccharides are then released from the complex by simple ligand exchange. [reaction: see text]
Pornsuriyasak
Papapida
P
Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, MO 63121, USA.
Gangadharmath
Umesh B
UB
Rath
Nigam P
NP
Demchenko
Alexei V
AV
D004187:Disaccharides / Q000138:chemical synthesis; D006027:Glycosides / Q000737:chemistry; D006031:Glycosylation; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010165:Palladium; D013844:Thiazoles / Q000737:chemistry
D004187:Disaccharides; D006027:Glycosides; D009844:Oligosaccharides; D013844:Thiazoles; D010165:Palladium