Synthesis and applications of a light-fluorous glycosyl donor.
A new method using a light-fluorous glycosyl donor and an orthogonal tagging strategy to synthesize oligosaccharides and glycoconjugates has been developed. The glycosyl donor orthogonally protected with a C8F17-silyl tag and benzoyl groups was reacted with excess amounts of glycosyl acceptor. Fluorous solid-phase extraction separated the glycosylated product and unreacted glycosyl acceptor. This new protocol has high reaction efficiency and easy separation, which was demonstrated in the synthesis of an unprotected trisaccharide and an O-glycosylated serine in this paper.
Zhang
Fa
F
Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, PR China.
Zhang
Wei
W
Zhang
Yan
Y
Curran
Dennis P
DP
Liu
Gang
G
D006001:Glycoconjugates / Q000138:chemical synthesis*; D006031:Glycosylation; D008722:Methods; D009844:Oligosaccharides / Q000138:chemical synthesis*; D052616:Solid Phase Extraction
D006001:Glycoconjugates; D009844:Oligosaccharides