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

doi:10.1021/ol402034g

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

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	4520-4523
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	17
DOIs	https://doi.org/10.1021/ol402034g
State	Published - 6 Sep 2013

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10.1021/ol402034g

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title = "Automated solution-phase synthesis of oligosaccharides via iterative electrochemical assembly of thioglycosides",

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.",

author = "Toshiki Nokami and Ryutaro Hayashi and Yoshihiro Saigusa and Akihiro Shimizu and Liu, {Chih Yueh} and Kwok-Kong Mong and Yoshida, {Jun Ichi}",

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Automated solution-phase synthesis of oligosaccharides via iterative electrochemical assembly of thioglycosides. / Nokami, Toshiki; Hayashi, Ryutaro; Saigusa, Yoshihiro; Shimizu, Akihiro; Liu, Chih Yueh; Mong, Kwok-Kong; Yoshida, Jun Ichi.

In: Organic Letters, Vol. 15, No. 17, 06.09.2013, p. 4520-4523.

Research output: Contribution to journal › Article › peer-review

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T1 - Automated solution-phase synthesis of oligosaccharides via iterative electrochemical assembly of thioglycosides

AU - Nokami, Toshiki

AU - Hayashi, Ryutaro

AU - Saigusa, Yoshihiro

AU - Shimizu, Akihiro

AU - Liu, Chih Yueh

AU - Mong, Kwok-Kong

AU - Yoshida, Jun Ichi

PY - 2013/9/6

Y1 - 2013/9/6

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