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

28 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 languageEnglish
Pages (from-to)4649-4652
Number of pages4
JournalOrganic Letters
Volume7
Issue number21
DOIs
Publication statusPublished - Oct 13 2005

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Dideoxynucleosides
Glycosylation
Electrooxidation
halides
cleavage
halos
Salts
salts
synthesis

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

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

Mitsudo, K, Kawaguchi, T, Miyahara, S, Matsuda, W, Kuroboshi, M & Tanaka, H 2005, 'Electrooxidative glycosylation through C-S bond cleavage of 1-arylthio-2,3-dideoxyglycosides. Synthesis of 2′,3′- dideoxynucleosides', Organic Letters, vol. 7, no. 21, pp. 4649-4652. https://doi.org/10.1021/ol051776d
Mitsudo K, Kawaguchi T, Miyahara S, Matsuda W, Kuroboshi M, Tanaka H. Electrooxidative glycosylation through C-S bond cleavage of 1-arylthio-2,3-dideoxyglycosides. Synthesis of 2′,3′- dideoxynucleosides. Organic Letters. 2005 Oct 13;7(21):4649-4652. https://doi.org/10.1021/ol051776d
Mitsudo, Koichi ; Kawaguchi, Takashi ; Miyahara, Seiji ; Matsuda, Wataru ; Kuroboshi, Manabu ; Tanaka, Hideo. / Electrooxidative glycosylation through C-S bond cleavage of 1-arylthio-2,3-dideoxyglycosides. Synthesis of 2′,3′- dideoxynucleosides. In: Organic Letters. 2005 ; Vol. 7, No. 21. pp. 4649-4652.
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AU - Kuroboshi, Manabu

AU - Tanaka, Hideo

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