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【结 构 式】 
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【分子编号】13123 【品名】(2R)-2-(2,4-Difluorophenyl)-2-[(1R)-1-phenoxyethyl]oxirane; (1R)-1-[(2R)-2-(2,4-Difluorophenyl)oxiranyl]ethyl phenyl ether 【CA登记号】 |
【 分 子 式 】C16H14F2O2 【 分 子 量 】276.2827664 【元素组成】C 69.56% H 5.11% F 13.75% O 11.58% |
合成路线1
该中间体在本合成路线中的序号：(VI)A synthesis of Sch-42427/SM-9164, the active (RR)-enantiomer of Sch-39304, has been reported: The reaction of the chiral epoxide 2-(2,4-difluorophenyl)-3(R)-methyloxirane (I) with trimethylsilyltriflate (TMSOTf) or tert-butyldimethylsilyl triflate (TBDMSOTf) yields compound (II) or (III), respectively; the acidic hydrolysis of both compounds affords the chiral ketol (IV), which is protected with dihydropyran (DHP) to give the tetrahydropyranyl ether (V). The regioselective reaction of (V) with trimethylsulfonium iodide and NaH in THF affords the chiral oxirane (VI), which is treated with sodium 1,2,4-triazole (VII) in DMF to afford the (R,R)-diol (VIII). Finally, this compound is partially esterified with methanesulfonyl chloride, treated with methylmercaptane, and finally oxidized with peracetic acid.
| 【1】 Gala, D.; DiBenedetto, D.J.; A rational approach to chiral alpha-hydroxy aryl ketones from chiral aryl epoxides via regioselective, stereo retentive oxidative epoxide opening: Its application to the synthesis of antifungal Sch 42427/SM 9164. Tetrahedron Lett 1994, 35, 45, 8299. |
| 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) | 13099 | (3R)-2-(2,4-Difluorophenyl)-3-methyloxirane | C9H8F2O | 详情 | 详情 | |
| (II) | 13119 | (2R)-1-(2,4-Difluorophenyl)-2-[(trimethylsilyl)oxy]-1-propanone | C12H16F2O2Si | 详情 | 详情 | |
| (III) | 13120 | (2R)-2-[[tert-Butyl(dimethyl)silyl]oxy]-1-(2,4-difluorophenyl)-1-propanone | C15H22F2O2Si | 详情 | 详情 | |
| (IV) | 13100 | (2R)-1-(2,4-Difluorophenyl)-2-hydroxy-1-propanone | C9H8F2O2 | 详情 | 详情 | |
| (V) | 13102 | (2R)-1-(2,4-Difluorophenyl)-2-(tetrahydro-2H-pyran-2-yloxy)-1-propanone | C14H16F2O3 | 详情 | 详情 | |
| (VI) | 13123 | (2R)-2-(2,4-Difluorophenyl)-2-[(1R)-1-phenoxyethyl]oxirane; (1R)-1-[(2R)-2-(2,4-Difluorophenyl)oxiranyl]ethyl phenyl ether | C16H14F2O2 | 详情 | 详情 | |
| (VII) | 13104 | 1,2,4-Triazole, sodium derivative | 41253-21-8 | C2H2N3Na | 详情 | 详情 |
| (VIII) | 13106 | (2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol | C12H13F2N3O2 | 详情 | 详情 |