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Synthesis 2003(1): 0107-0111
DOI: 10.1055/s-2003-36249
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of AZT 5′-O-Hydrogen Phospholipids [1] and their Derivatives

Qiang Xiaoa, Jing Sunb, Qi Suna, Yong Ju*a, Yu-fen Zhao*a, Yu-xin Cuib
a The Key Laboratory of Bioorganic Phosphorus Chemistry, Ministry of Education, Department of Chemistry, School of Life Sciences and Engineering, Tsinghua University, Beijing 100084, P. R. China
b National Research Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100083, P. R. China
Fax: +86(10)62781695; e-Mail: juyong@tsinghua.edu.cn; e-Mail: yfzhao@tsinghua.edu.cn;
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Publication History

Received 10 September 2002
Publication Date:
18 December 2002 (online)

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Abstract

A series of AZT 5′-O-hydrogen phospholipids 5a-e were synthesized by a tandem transesterification of diphenyl phosphite (DPP) with AZT and a long-chain alcohol. This method has the merits of easy operation and high yields. The corresponding phosphonates, phosphorothionates and phosphoroselenoates of 5d and 5e and the phosphoramidates conjugated with l-amino acid methyl ester 9a and 9b were also synthesized.

Key words

phosphorylations - transesterification - phosphonate - antiviral agents - nucleosides - phospholipids - phosphorus

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