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Synlett 2000; 2000(5): 0671-0673
DOI: 10.1055/s-2000-6640
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Chlorination of Nucleosides by N-chlorodiisopropylamine and Triphenylphosphine

Yi-Sui Zhou* , Z.-W. Miao, Yu-Fen Zhao
  • *Bioorganic Phosphorus Chemistry Laboratory, Department of Chemistry, School of life science and Engineering, Tsinghua University, Beijing, 100084, P.R. China; Fax 010-62781695; E-mail: tp-dch@mail.tsinghua.edu.cn
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Publication Date:
31 December 2000 (online)

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The combination of N-chlorodiisopropylamine and triphenylphosphine (1) was exploited as a new method for chlorination of the hydroxyl group on the nucleosides. A possible mechanism involving an oxyphosphonium intermediate 2a and a phosphorane intermediate 2b was proposed based on the results from 31P NMR spectrum.

chlorination - NMR - nucleosides