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*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)


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
Issue number6
Publication statusPublished - 2004
Externally publishedYes


  • 5′-Thionucleoside
  • Chlorination
  • Cycloisoguanosine
  • Isoguanosine

ASJC Scopus subject areas

  • General Chemistry


Dive into the research topics of 'Nucleosides XII.1 synthesis of 5′-modified isoguanosines and reinvestigation of 5′-deoxy-N3,5′-cycloisoguanosine'. Together they form a unique fingerprint.

Cite this