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Synlett 2005(16): 2537-2539  
DOI: 10.1055/s-2005-917085
LETTER
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Aryl Phosphoramidate Derivatives of AZT/d4T as Anti-HIV Prodrugs

Peng Jianga, Xin Guoa, Hua Fu*a, Yuyang Jianga,b, Yufen Zhaoa
a Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
Fax: +86(10)62781695; e-Mail: fuhua@mail.tsinghua.edu.cn;
b Key Laboratory of Chemical Biology, Guangdong Province, Graduate School of Shenzhen, Tsinghua University, Shenzhen 518057, P. R. of China
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Publication History

Received 28 July 2005
Publication Date:
21 September 2005 (online)

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Abstract

Arbuzov reaction of aryl phosphorodichloridite with mixture of one equivalent of AZT or d4T and one equivalent of tert-butyl alcohol led to the corresponding AZT/d4T aryl H-phos­phonate diesters, and the following reaction of the H-phosphonate diesters with amino acid methyl esters in the presence of N-chlorosuccinimide (NCS) produced membrane-soluble anti-HIV prodrugs AZT/d4T aryl phosphoramidate derivatives in good yields.

Key words

aryl phosphoramidate derivatives - anti-HIV prodrugs - N-chlorosuccinimide (NCS) - AZT - d4T

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