New and One Pot Chemoselective Synthesis of Nucleoside 5′-H-Phosphonate Diesters

Xin Guo Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing, P.R. China

Peng Jiang Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing, P.R. China

Hua Fu Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing, P.R. China

Yuyang Jiang Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing, P.R. China; Key Laboratory of Chemical Biology, Guangdong Province, Graduate School of Shenzhen, Tsinghua University, Shenzhen, P.R. China

Yufen Zhao Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing, P.R. China

Abstract

Arbuzov reaction of phenyl phosphorodichloridite with two equiv of alcohol, or mixture of one equiv of alcohol and one equiv of tert-butyl alcohol, led to the corresponding aryl H-phosphonate diesters. Following displacement of the H-phosphonate diesters with unprotected nucleosides chemoselectively produced nucleoside 5′-H-phosphonate diesters in good yields, respectively.

Keywords:

The program is supported from the Excellent Dissertation Foundations by the Chinese Ministry of Education (No. 200222), the Excellent Young Teacher Program of MOE, P. R. China, and the National Natural Science Foundation of China (Grand No. 20472042).

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New and One Pot Chemoselective Synthesis of Nucleoside 5′-H-Phosphonate Diesters

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New and One Pot Chemoselective Synthesis of Nucleoside 5′-H-Phosphonate Diesters

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