Synthesis of AZT/d4T Boranophosphates as Anti-HIV Prodrug Candidates

Changxue Lin; Hua Fu; Guangzhong Tu; Yufen Zhao

doi:10.1055/s-2004-815939

PAPER

Synthesis of AZT/d4T Boranophosphates as Anti-HIV Prodrug Candidates

Changxue Lin^a, Hua Fu*^a, Guangzhong Tu^b, Yufen Zhao*^a
^a 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
e-Mail: fuhua@mail.tsinghua.edu.cn;
^b Beijing Institute of Microchemistry, Beijing 100091, P. R. China

Abstract

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Abstract

AZT/d4T phosphonates were synthesized by sequential condensation of AZT/d4T with the corresponding alcohols or 5′-DMT-thymidine in the presence of pivaloyl chloride. Sequential silylation, boronation, and hydrolysis in ammonium hydroxide of these phosphonates led to anti-HIV prodrug candidates AZT/d4T boranophosphates.

Key words

anti-HIV - AZT - d4T - phosphonate - boranophosphate

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