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

31 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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Electrooxidative glycosylation through C-S bond cleavage of 1-arylthio-2,3-dideoxyglycosides. Synthesis of 2′,3′- dideoxynucleosides. / Mitsudo, Koichi; Kawaguchi, Takashi; Miyahara, Seiji; Matsuda, Wataru; Kuroboshi, Manabu; Tanaka, Hideo.

In: Organic Letters, Vol. 7, No. 21, 13.10.2005, p. 4649-4652.

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

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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",

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

Abstract

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