A General and Chemoselective Synthesis of Phosphoramidates through Reaction of Silylated Nucleoside Di- and Triphosphates with Silylated Amines Containing Multifunctional Groups

Jigang Zhu,† Hua Fu,*† Yuyang Jiang,†‡ and Yufen Zhao†
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China, and Key Laboratory of Chemical Biology, Guangdong Province, Graduate School of Shenzhen, Tsinghua University, Shenzhen 518057, P. R. China fuhua@mail.tsinghua.edu.cn
J. Org. Chem., 2006, 71 (4), pp 1722–1724
DOI: 10.1021/jo0521403
Publication Date (Web): January 17, 2006
Copyright © 2006 American Chemical Society
†

 Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology.

,
*

 To whom correspondence should be addressed. Fax:  86-10-62781695.

,
‡

 Key Laboratory of Chemical Biology.

Abstract

Abstract Image

An approach to various phosphoramidates has been developed through one-pot chemoselective reaction of nucleoside di- and triphosphates with 3‘-amino-3‘-deoxythymidine, d-glucosamine, and peptides mediated by trimethylsilyl chloride, and the corresponding conjugates via the linkage of phosphate were obtained. The method could be generally applied for the synthesis of phosphoramidates without any preprotection of polyphosphates and amines containing multifunctional groups.

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History

  • Published In Issue February 17, 2006
  • Received October 13, 2005

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