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

研究成果: 雜誌貢獻期刊論文同行評審

4 引文 斯高帕斯(Scopus)

摘要

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.

原文英語
頁(從 - 到)1401-1406
頁數6
期刊Journal of the Chinese Chemical Society
51
發行號6
DOIs
出版狀態已發佈 - 2004

ASJC Scopus subject areas

  • Chemistry(all)

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