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【结 构 式】 
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【分子编号】38697 【品名】(2S)-2-[(3aS,7S,7aR)-3a-methyl-7-[(trimethylsilyl)oxy]-3a,4,5,6,7,7a-hexahydro-1H-inden-3-yl]-6-[[tert-butyl(dimethyl)silyl]oxy]-6-methyl-4-heptyn-3-ol 【CA登记号】 |
【 分 子 式 】C27H50O3Si2 【 分 子 量 】478.8632 【元素组成】C 67.72% H 10.52% O 10.02% Si 11.73% |
合成路线1
该中间体在本合成路线中的序号：(XVI)Alternatively, the intermediate diol (IX) has been obtained as follows: The condensation of perhydroindene derivative (XIV) with the acetylenic aldehyde (XV) by means of Me3AlCl gives the acetylenic alcohol (XVI), which is esterified to the formate (XVII) or the carbonate (XVIII). The deoxygenation of (XVII) or (XVIII) by means of Pd(acac)2 and P(CH3)3 in hot toluene affords the silylated diol (XIX), which is submitted to desilylation with TBAF to afford the target diol intermediate (IX).
| 【1】 Radinov, R.; Hutchings, S.D.; Selective palladium-catalyzed hydrogenolysis of a secondary propargylic alcohol in the synthesis of vitamin D analog Ro 23-7553: Substrate and ligand control. Tetrahedron Lett 1999, 40, 51, 8955. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX) | 38690 | (3aS,7S,7aR)-3-[(1R)-5-hydroxy-1,5-dimethyl-3-hexynyl]-3a-methyl-3a,4,5,6,7,7a-hexahydro-1H-inden-7-ol | C18H28O2 | 详情 | 详情 | |
| (XIV) | 38695 | (3aR,4S,7aS)-1-[(Z)ethylidene]-7a-methyloctahydro-1H-inden-4-yl trimethylsilyl ether; ([(3aR,4S,7aS)-1-[(Z)ethylidene]-7a-methyloctahydro-1H-inden-4-yl]oxy)(trimethyl)silane | C15H28OSi | 详情 | 详情 | |
| (XV) | 38696 | 4-[[tert-butyl(dimethyl)silyl]oxy]-4-methyl-2-pentynal | C12H22O2Si | 详情 | 详情 | |
| (XVI) | 38697 | (2S)-2-[(3aS,7S,7aR)-3a-methyl-7-[(trimethylsilyl)oxy]-3a,4,5,6,7,7a-hexahydro-1H-inden-3-yl]-6-[[tert-butyl(dimethyl)silyl]oxy]-6-methyl-4-heptyn-3-ol | C27H50O3Si2 | 详情 | 详情 | |
| (XVII) | 38698 | 1-((1S)-1-[(3aS,7S,7aR)-3a-methyl-7-[(trimethylsilyl)oxy]-3a,4,5,6,7,7a-hexahydro-1H-inden-3-yl]ethyl)-4-[[tert-butyl(dimethyl)silyl]oxy]-4-methyl-2-pentynyl formate | C28H50O4Si2 | 详情 | 详情 | |
| (XVIII) | 38699 | 1-((1S)-1-[(3aS,7S,7aR)-3a-methyl-7-[(trimethylsilyl)oxy]-3a,4,5,6,7,7a-hexahydro-1H-inden-3-yl]ethyl)-4-[[tert-butyl(dimethyl)silyl]oxy]-4-methyl-2-pentynyl methyl carbonate | C29H52O5Si2 | 详情 | 详情 | |
| (XIX) | 38700 | [((5R)-5-[(3aS,7S,7aR)-3a-methyl-7-[(trimethylsilyl)oxy]-3a,4,5,6,7,7a-hexahydro-1H-inden-3-yl]-1,1-dimethyl-2-hexynyl)oxy](tert-butyl)dimethylsilane; (5R)-5-[(3aS,7S,7aR)-3a-methyl-7-[(trimethylsilyl)oxy]-3a,4,5,6,7,7a-hexahydro-1H-inden-3-yl]-1,1-dimethyl-2-hexynyl tert-butyl(dimethyl)silyl ether | C27H50O2Si2 | 详情 | 详情 |