Citation: Yi SHEN, Ling XIANG, Yong DENG, Yu Guo ZHONG. A Convenient Synthesis of cis and trans-(±)-4-Amino-1-[2-(hydroxyl-methyl)-1, 3-oxathiolan-5-yl]-2(1H)-pyrimidinone[J]. Chinese Chemical Letters, ;2006, 17(4): 431-433. shu

A Convenient Synthesis of cis and trans-(±)-4-Amino-1-[2-(hydroxyl-methyl)-1, 3-oxathiolan-5-yl]-2(1H)-pyrimidinone

Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041

Received Date: 5 September 2005

Fund Project: This work was supported by the National High Technology Research and Development Program of China (863 project: 2003AA2Z3154).

A convenient synthesis of cis-(±) isomer 1 and trans-(±) isomer 2 of lamivudine starting from benzoyloxyacetaldehyde and 1, 4-dithiane-2, 5-diol is described. The key steps include chlorination of oxathiolane lactol 5 by SOCl₂/DMF, followed by coupling with silylated N⁴-acetylcytosine and deprotection. The overall yield was 42.6% and 20.1%, respectively.
- Lamivudine,
- geometrical isomer,
- cis-(±) isomer,
- trans-(±) isomer,
- synthesis
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