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【结 构 式】 
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【分子编号】52502 【品名】bis(2,2,2-trifluoroethyl) {[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]oxy}methylphosphonate 【CA登记号】 |
【 分 子 式 】C12H13ClF6N5O4P 【 分 子 量 】471.6834012 【元素组成】C 30.56% H 2.78% Cl 7.52% F 24.17% N 14.85% O 13.57% P 6.57% |
合成路线1
该中间体在本合成路线中的序号：(VI)Phosphonate (III) was prepared by the Michaelis-Arbuzov reaction by heating a mixture of 2-chloroethyl chloromethyl ether (I) and tris(2,2,2-trifluoroethyl)phosphite (II) at 160 C. The chloroethoxy derivative (III) was then converted to the corresponding iodide (IV) by treatment with NaI under Finkelstein reaction conditions. Alkylation of 2-amino-6-chloropurine (V) with iodide (IV) in the presence of DBU furnished the phosphonyl purine (VI). The 6-chloro group of (VI) was finally displaced with p-methoxythiophenol (VII) in hot DMF, yielding the target thioether.
| 【1】 Ubasawa, M.; Kamiya, N.; Takashima, H.; Yuasa, S.; Ueda, N.; Sekiya, K. (Mitsubishi Chemical Corp.); Phosphonate nucleotide cpds.. EP 0785208; US 5840716 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 36041 | 2-chloroethyl chloromethyl ether; 1-chloro-2-(chloromethoxy)ethane | 1462-33-5 | C3H6Cl2O | 详情 | 详情 |
| (II) | 52499 | Tris(2,2,2-trifluoroethyl)phosphite | C6H6F9O3P | 详情 | 详情 | |
| (III) | 52500 | bis(2,2,2-trifluoroethyl) [(2-chloroethyl)oxy]methylphosphonate | C7H10ClF6O4P | 详情 | 详情 | |
| (IV) | 52501 | bis(2,2,2-trifluoroethyl) [(2-iodoethyl)oxy]methylphosphonate | C7H10F6IO4P | 详情 | 详情 | |
| (V) | 11644 | 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine | 10310-21-1 | C5H4ClN5 | 详情 | 详情 |
| (VI) | 52502 | bis(2,2,2-trifluoroethyl) {[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]oxy}methylphosphonate | C12H13ClF6N5O4P | 详情 | 详情 | |
| (VII) | 25639 | 4-methoxyphenylhydrosulfide; 4-methoxybenzenethiol | 34320-82-6 | C7H8OS | 详情 | 详情 |