Nucleosides XII.1 synthesis of 5′-modified isoguanosines and reinvestigation of 5′-deoxy-N3,5′-cycloisoguanosine

Tun Cheng Chien, Chia Chi Kuo, Chien Shu Chen, Ji Wang Chern

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Isoguanosine (3) underwent a coupling reaction with diaryl disulfides in the presence of tri-n-butylphosphine when its 6-amino group was protected by N,N-dimethylaminomethylidene. The synthesis of 5′-deoxy-N 3,5′-cycloisoguanosine (6) and its 2′,3′-O- isopropylidene derivative (11) were accomplished in excellent yields from isoguanosines (3 & 10) in the presence of triphenylphospine and carbon tetrachloride in pyridine. Chlorination at the 5′-position of isoguanosine (3) with thionyl chloride followed by the aqueous base-promoted cyclization afforded the same product 6. The structures were elucidated by spectroscopic analysis including IR, UV, 1-D and 2-D NMR.

Original languageEnglish
Pages (from-to)1401-1406
Number of pages6
JournalJournal of the Chinese Chemical Society
Volume51
Issue number6
DOIs
Publication statusPublished - 2004 Jan 1

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Nucleosides
Spectroscopic analysis
Carbon Tetrachloride
Chlorination
Cyclization
Disulfides
Nuclear magnetic resonance
Derivatives
isoguanosine

Keywords

  • 5′-Thionucleoside
  • Chlorination
  • Cycloisoguanosine
  • Isoguanosine

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Nucleosides XII.1 synthesis of 5′-modified isoguanosines and reinvestigation of 5′-deoxy-N3,5′-cycloisoguanosine. / Chien, Tun Cheng; Kuo, Chia Chi; Chen, Chien Shu; Chern, Ji Wang.

In: Journal of the Chinese Chemical Society, Vol. 51, No. 6, 01.01.2004, p. 1401-1406.

Research output: Contribution to journalArticle

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AU - Kuo, Chia Chi

AU - Chen, Chien Shu

AU - Chern, Ji Wang

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N2 - Isoguanosine (3) underwent a coupling reaction with diaryl disulfides in the presence of tri-n-butylphosphine when its 6-amino group was protected by N,N-dimethylaminomethylidene. The synthesis of 5′-deoxy-N 3,5′-cycloisoguanosine (6) and its 2′,3′-O- isopropylidene derivative (11) were accomplished in excellent yields from isoguanosines (3 & 10) in the presence of triphenylphospine and carbon tetrachloride in pyridine. Chlorination at the 5′-position of isoguanosine (3) with thionyl chloride followed by the aqueous base-promoted cyclization afforded the same product 6. The structures were elucidated by spectroscopic analysis including IR, UV, 1-D and 2-D NMR.

AB - Isoguanosine (3) underwent a coupling reaction with diaryl disulfides in the presence of tri-n-butylphosphine when its 6-amino group was protected by N,N-dimethylaminomethylidene. The synthesis of 5′-deoxy-N 3,5′-cycloisoguanosine (6) and its 2′,3′-O- isopropylidene derivative (11) were accomplished in excellent yields from isoguanosines (3 & 10) in the presence of triphenylphospine and carbon tetrachloride in pyridine. Chlorination at the 5′-position of isoguanosine (3) with thionyl chloride followed by the aqueous base-promoted cyclization afforded the same product 6. The structures were elucidated by spectroscopic analysis including IR, UV, 1-D and 2-D NMR.

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