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Citation: Wang Yongsheng, Zhao Ling, Liu Rong. A New Synthesis Method for Fiacitabine[J]. Chemistry, ;2020, 83(1): 88-91. shu

A New Synthesis Method for Fiacitabine

1.
Gansu Key Laboratory of Fine Chemicals, Lanzhou, 730020
2.
Gansu Chemical Industry Research Institute Co., Ltd., Lanzhou, 730020
3.
Department of Pathology, Lanzhou University Second Hospital, Lanzhou, 730030

Received Date: 2 August 2019
Accepted Date: 12 October 2019

Figures(1)

Fiacitabine (FIAC) is a pyrimidine nucleoside analog with activity against various herpesviruses. In this paper, ((2R, 3S, 4S)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate (4) is afforded in high yields through brominiation, starting with (2R, 3S, 4R, 5R)-5-(benzoyloxymethyl)-3-fluorotetrahydrofuran-2, 4-dily dibenzoate at room temperature; and simultaneously N-(5-iodo-1, 2-dihydropyrimidin-4-yl)benzamind (5) was effectively synthesized through two steps including iodobenzene, Bz-protection, starting with cytosine, which can be obtained cheaply and conveniently. Then FIAC is obtained by substitution reaction with intermediate 4 and 5 followed by deprotection reaction. This synthetic route has the advantages of brief reaction steps, convenient manipulation and high product selectivity for FIAC. The overall yield is 43%.
- Fiacitabine,
- Benzoyl oxide,
- Cytosine,
- Synthesis
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