Browsing by Author "Nokami, Toshiki"

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Automated Solution-Phase Synthesis of Oligosaccharides via Iterative Electrochemical Assembly of Thioglycosides
(2013-09-06)
Nokami, Toshiki
;
Hayashi, Ryutaro
;
Saigusa, Yoshihiro
;
Shimizu, Akihiro
;
Liu, Chih-Yueh
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.
Chemical Glycosylation by Single Electron Transfer
(2015-04-01)
Nokami, Toshiki
;
Itoh, Toshiyuki
;
Mong, Kwok-Kong Tony
;
應用化學系
;
Department of Applied Chemistry
Oligosaccharides play important roles in nature; however, chemical synthesis of oligosaccharides is still difficult and not carried out in a fully automated manner. Among various methods, the activation of glycosyl donors by single electron transfer using electrochemical and photochemical methods has several benefits. In particular, electrochemical oxidation is a powerful method to activate glycosyl donors, including thioglycosides, which are one of the most popular class of glycosyl donors in modern chemical glycosylations. This review article covers the pioneering works of electrochemical glycosylations, other chemical glycosylations achieved by single electron transfer, and our recent approach to the automated solution-phase synthesis of oligosaccharides based on the electrochemical method.