Nucleosides. IX. Synthesis of Purine N3,5′ -Cyclonucleosides and N3,5′-Cyclo-2′,3′ -seconucleosides via Mitsunobu Reaction as TIBO-like Derivativest

Grace Shiahuy Chen, Chien Shu Chen, Tun-Cheng Chien, Jun Yen Yeh, Chia Chi Kuo, Rahul Subhash Talekar, Ji Wang Chern

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The Mitsunobu reaction was applied to prepare, in one step, purine N 3,5′-cyclonucleosides 10a-d. A subsequent ring opening in the ribose moiety of the resultant N3,5′-nucleosides by sodium periodate led to the corresponding N3,5′-cyclo-2′ ,3′-seconucleosides. These products consist of 5-, 6-, and 7-membered tricyclic system which is the basic skeleton of TIBO derivatives, known antiviral agents.

Original languageEnglish
Pages (from-to)347-359
Number of pages13
JournalNucleosides, Nucleotides and Nucleic Acids
Volume23
Issue number1-2
DOIs
Publication statusPublished - 2004 Mar 26

Fingerprint

Ribose
Nucleosides
Skeleton
Antiviral Agents
Derivatives
cyclo 3
metaperiodate
purine

Keywords

  • Formycin B
  • Mitsunobu reaction
  • N ,5′-cyclo-2′, 3′-seconucleoside
  • N,5′-cyclonucleoside
  • TIBO

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Genetics

Cite this

Nucleosides. IX. Synthesis of Purine N3,5′ -Cyclonucleosides and N3,5′-Cyclo-2′,3′ -seconucleosides via Mitsunobu Reaction as TIBO-like Derivativest. / Chen, Grace Shiahuy; Chen, Chien Shu; Chien, Tun-Cheng; Yeh, Jun Yen; Kuo, Chia Chi; Talekar, Rahul Subhash; Chern, Ji Wang.

In: Nucleosides, Nucleotides and Nucleic Acids, Vol. 23, No. 1-2, 26.03.2004, p. 347-359.

Research output: Contribution to journalArticle

Chen, Grace Shiahuy ; Chen, Chien Shu ; Chien, Tun-Cheng ; Yeh, Jun Yen ; Kuo, Chia Chi ; Talekar, Rahul Subhash ; Chern, Ji Wang. / Nucleosides. IX. Synthesis of Purine N3,5′ -Cyclonucleosides and N3,5′-Cyclo-2′,3′ -seconucleosides via Mitsunobu Reaction as TIBO-like Derivativest. In: Nucleosides, Nucleotides and Nucleic Acids. 2004 ; Vol. 23, No. 1-2. pp. 347-359.
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