Electrooxidative glycosylation through C-S bond cleavage of 1-arylthio-2,3-dideoxyglycosides. Synthesis of 2′,3′- dideoxynucleosides

Koichi Mitsudo; Takashi Kawaguchi; Seiji Miyahara; Wataru Matsuda; Manabu Kuroboshi; Hideo Tanaka

doi:10.1021/ol051776d

Electrooxidative glycosylation through C-S bond cleavage of 1-arylthio-2,3-dideoxyglycosides. Synthesis of 2′,3′- dideoxynucleosides

Koichi Mitsudo, Takashi Kawaguchi, Seiji Miyahara, Wataru Matsuda, Manabu Kuroboshi, Hideo Tanaka

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

34 Citations (Scopus)

Abstract

(Chemical Equation Presented) The electrooxidative glycosylation of newly designed 1-arylthio-substituted 2,3-dideoxyglycosides is described. The halide salt-mediated electrooxidation utilizing either of the α- or β-thiodideoxyglycosides proceeded smoothly at -78°C to give dideoxynucleosides in a β-selective manner, presumably through a 1-halo-substituted glycosyl donor.

Original language	English
Pages (from-to)	4649-4652
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	21
DOIs	https://doi.org/10.1021/ol051776d
Publication status	Published - Oct 13 2005

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol051776d

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title = "Electrooxidative glycosylation through C-S bond cleavage of 1-arylthio-2,3-dideoxyglycosides. Synthesis of 2′,3′- dideoxynucleosides",

abstract = "(Chemical Equation Presented) The electrooxidative glycosylation of newly designed 1-arylthio-substituted 2,3-dideoxyglycosides is described. The halide salt-mediated electrooxidation utilizing either of the α- or β-thiodideoxyglycosides proceeded smoothly at -78°C to give dideoxynucleosides in a β-selective manner, presumably through a 1-halo-substituted glycosyl donor.",

author = "Koichi Mitsudo and Takashi Kawaguchi and Seiji Miyahara and Wataru Matsuda and Manabu Kuroboshi and Hideo Tanaka",

year = "2005",

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language = "English",

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T1 - Electrooxidative glycosylation through C-S bond cleavage of 1-arylthio-2,3-dideoxyglycosides. Synthesis of 2′,3′- dideoxynucleosides

AU - Mitsudo, Koichi

AU - Kawaguchi, Takashi

AU - Miyahara, Seiji

AU - Matsuda, Wataru

AU - Kuroboshi, Manabu

AU - Tanaka, Hideo

PY - 2005/10/13

Y1 - 2005/10/13

N2 - (Chemical Equation Presented) The electrooxidative glycosylation of newly designed 1-arylthio-substituted 2,3-dideoxyglycosides is described. The halide salt-mediated electrooxidation utilizing either of the α- or β-thiodideoxyglycosides proceeded smoothly at -78°C to give dideoxynucleosides in a β-selective manner, presumably through a 1-halo-substituted glycosyl donor.

AB - (Chemical Equation Presented) The electrooxidative glycosylation of newly designed 1-arylthio-substituted 2,3-dideoxyglycosides is described. The halide salt-mediated electrooxidation utilizing either of the α- or β-thiodideoxyglycosides proceeded smoothly at -78°C to give dideoxynucleosides in a β-selective manner, presumably through a 1-halo-substituted glycosyl donor.

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JF - Organic Letters

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Electrooxidative glycosylation through C-S bond cleavage of 1-arylthio-2,3-dideoxyglycosides. Synthesis of 2′,3′- dideoxynucleosides

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