Automated solution-phase synthesis of oligosaccharides via iterative electrochemical assembly of thioglycosides

Toshiki Nokami*, Ryutaro Hayashi, Yoshihiro Saigusa, Akihiro Shimizu, Chih Yueh Liu, Kwok-Kong Mong, Jun Ichi Yoshida

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

58 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)4520-4523
Number of pages4
JournalOrganic Letters
Volume15
Issue number17
DOIs
StatePublished - 6 Sep 2013

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