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【结 构 式】 
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【分子编号】44266 【品名】(3aR,7aS)-7a-methyl-1-[(1R,3E)-6,6,6-trifluoro-5-hydroxy-1-methyl-5-(trifluoromethyl)-3-hexenyl]-3,3a,5,6,7,7a-hexahydro-4H-inden-4-one 【CA登记号】 |
【 分 子 式 】C18H22F6O2 【 分 子 量 】384.3618992 【元素组成】C 56.25% H 5.77% F 29.66% O 8.33% |
合成路线1
该中间体在本合成路线中的序号：(III)Reduction of the triple bond of compound (I) with LiAlH4 in the presence of NaOMe furnished the E-olefin (II). The secondary alcohol group of (II) was then oxidized to the corresponding ketone (III) by means of pyridinium dichromate in the presence of pyridinium p-toluenesulfonate. Condensation of this ketone with the ylide resulting from phosphine oxide (IV) and n-BuLi produced the silylated cholecalciferol analogue (V). The silyl protecting groups of (V) were finally removed by treatment with tetrabutylammonium fluoride.
| 【1】 Doran, T.I.; Hennessy, B.M.; McLane, J.A.; Pizzolato, G.; Sedarati, F.; Uskokovic, M.R. (F. Hoffmann-La Roche AG); Vitamin D3 analogs. EP 0654467; JP 1995188159; US 5428029 . |
| 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) | 30300 | (3aS,7S,7aR)-3a-methyl-3-[(1R)-6,6,6-trifluoro-5-hydroxy-1-methyl-5-(trifluoromethyl)-3-hexynyl]-3a,4,5,6,7,7a-hexahydro-1H-inden-7-ol | C18H22F6O2 | 详情 | 详情 | |
| (II) | 44265 | (3aS,7S,7aR)-3a-methyl-3-[(1R,3E)-6,6,6-trifluoro-5-hydroxy-1-methyl-5-(trifluoromethyl)-3-hexenyl]-3a,4,5,6,7,7a-hexahydro-1H-inden-7-ol | C18H24F6O2 | 详情 | 详情 | |
| (III) | 44266 | (3aR,7aS)-7a-methyl-1-[(1R,3E)-6,6,6-trifluoro-5-hydroxy-1-methyl-5-(trifluoromethyl)-3-hexenyl]-3,3a,5,6,7,7a-hexahydro-4H-inden-4-one | C18H22F6O2 | 详情 | 详情 | |
| (IV) | 30302 | [2-((3R,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]cyclohexylidene)ethyl](oxo)diphenylphosphorane; 2-((3R,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]cyclohexylidene)ethyl(diphenyl)phosphine oxide | C32H51O3PSi2 | 详情 | 详情 | |
| (V) | 44267 | (1R,5R)-3-[2-((3aS,7aS)-7a-methyl-1-[(1R,3E)-6,6,6-trifluoro-1-methyl-5-(trifluoromethyl)-5-[(trimethylsilyl)oxy]-3-hexenyl]-3,3a,5,6,7,7a-hexahydro-4H-inden-4-ylidene)ethylidene]-5-[[tert-butyl(dimethyl)silyl]oxy]cyclohexyl tert-butyl(dimethyl)sily; [((1R,5R)-3-[2-((3aS,7aS)-7a-methyl-1-[(1R,3E)-6,6,6-trifluoro-1-methyl-5-(trifluoromethyl)-5-[(trimethylsilyl)oxy]-3-hexenyl]-3,3a,5,6,7,7a-hexahydro-4H-inden-4-ylidene)ethylidene]-5-[[tert-butyl(dimethyl)silyl]oxy]cyclohexyl)oxy](tert-butyl)dimeth | C41H70F6O3Si3 | 详情 | 详情 |