Automated Solution-Phase Synthesis of Oligosaccharides via Iterative Electrochemical Assembly of Thioglycosides

作者:Nokami Toshiki*; Hayashi Ryutaro; Saigusa Yoshihiro; Shimizu Akihiro; Liu Chih Yueh; Mong Kwok Kong Tony; Yoshida Jun ichi
来源:Organic Letters, 2013, 15(17): 4520-4523.
DOI:10.1021/ol402034g

摘要

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-beta-D-(1-6)-N-acetylglucosamine.

  • 出版日期2013-9-6