Generation of alkoxycarbenium ion pools from thioacetals and applications to glycosylation chemistry

Shinkiti Suzuki; Kouichi Matsumoto; Kohsuke Kawamura; Seiji Suga; Jun Ichi Yoshida

doi:10.1021/ol048524h

Generation of alkoxycarbenium ion pools from thioacetals and applications to glycosylation chemistry

Shinkiti Suzuki, Kouichi Matsumoto, Kohsuke Kawamura, Seiji Suga, Jun Ichi Yoshida

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

83 Citations (Scopus)

Abstract

(Chemical Equation Presented) Alkoxycarbenium ions have been generated and accumulated as "cation pools" by the low-temperature electrochemical oxidation of α-phenylthioethers. Although an unsuccessful attempt to accumulate glycosyl cations was made, a one-pot method for electrochemical glycosylation, which involves anodic oxidation of thioglycosides to generate glycosyl cation equivalents followed by their reactions with glycosyl acceptors, has been developed.

Original language	English
Pages (from-to)	3755-3758
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	21
DOIs	https://doi.org/10.1021/ol048524h
Publication status	Published - Oct 14 2004
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol048524h

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abstract = "(Chemical Equation Presented) Alkoxycarbenium ions have been generated and accumulated as {"}cation pools{"} by the low-temperature electrochemical oxidation of α-phenylthioethers. Although an unsuccessful attempt to accumulate glycosyl cations was made, a one-pot method for electrochemical glycosylation, which involves anodic oxidation of thioglycosides to generate glycosyl cation equivalents followed by their reactions with glycosyl acceptors, has been developed.",

author = "Shinkiti Suzuki and Kouichi Matsumoto and Kohsuke Kawamura and Seiji Suga and Yoshida, {Jun Ichi}",

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T1 - Generation of alkoxycarbenium ion pools from thioacetals and applications to glycosylation chemistry

AU - Suzuki, Shinkiti

AU - Matsumoto, Kouichi

AU - Kawamura, Kohsuke

AU - Suga, Seiji

AU - Yoshida, Jun Ichi

PY - 2004/10/14

Y1 - 2004/10/14

N2 - (Chemical Equation Presented) Alkoxycarbenium ions have been generated and accumulated as "cation pools" by the low-temperature electrochemical oxidation of α-phenylthioethers. Although an unsuccessful attempt to accumulate glycosyl cations was made, a one-pot method for electrochemical glycosylation, which involves anodic oxidation of thioglycosides to generate glycosyl cation equivalents followed by their reactions with glycosyl acceptors, has been developed.

AB - (Chemical Equation Presented) Alkoxycarbenium ions have been generated and accumulated as "cation pools" by the low-temperature electrochemical oxidation of α-phenylthioethers. Although an unsuccessful attempt to accumulate glycosyl cations was made, a one-pot method for electrochemical glycosylation, which involves anodic oxidation of thioglycosides to generate glycosyl cation equivalents followed by their reactions with glycosyl acceptors, has been developed.

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Generation of alkoxycarbenium ion pools from thioacetals and applications to glycosylation chemistry

Abstract

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