Synthesis of 2′,3′-dideoxynucleosides via C-S bond cleavage: N-glycosylation of 2,3-dideoxy-1-[(2-pyridylmethyl)thio]glycoside

Koichi Mitsudo, Wataru Matsuda, Seiji Miyahara, Hideo Tanaka

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

N-Glycosylation of 2,3-dideoxy-1-[(2-pyridylmethyl)thio]glycosides (1a) using several activators is described. NBS-promoted glycosylation reaction utilizing either the α- or β-thiodideoxyglycoside proceeded smoothly at -78 °C to give the corresponding dideoxynucleoside in a β-selective manner, presumably through a common glycosyl donor.

Original languageEnglish
Pages (from-to)5147-5150
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number29
DOIs
Publication statusPublished - Jul 17 2006

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Dideoxynucleosides
Glycosylation
Glycosides

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of 2′,3′-dideoxynucleosides via C-S bond cleavage : N-glycosylation of 2,3-dideoxy-1-[(2-pyridylmethyl)thio]glycoside. / Mitsudo, Koichi; Matsuda, Wataru; Miyahara, Seiji; Tanaka, Hideo.

In: Tetrahedron Letters, Vol. 47, No. 29, 17.07.2006, p. 5147-5150.

Research output: Contribution to journalArticle

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