Automated solution-phase synthesis of oligosaccharides via iterative electrochemical assembly of thioglycosides.
A new iterative one-pot sequential method for the solution-phase synthesis of oligosaccharides has been devised on the basis of the electrochemical oxidation of a propagating thioglycoside terminus to generate the corresponding triflate, followed by the reaction with a thioglycoside building block having a free hydroxyl group. A practical automated synthesizer was developed for the method and was effectively used for assembling up to six thioglycoside building blocks to synthesize partial structures of poly-β-D-(1-6)-N-acetylglucosamine.
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyoku, Kyoto 615-8510, Japan. tnokami@chem.tottori-u.ac.jp
Toshiki
T
Nokami
Ryutaro
R
Hayashi
Yoshihiro
Y
Saigusa
Akihiro
A
Shimizu
Chih-Yueh
CY
Liu
Kwok-Kong Tony
KK
Mong
Jun-ichi
J
Yoshida