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【结 构 式】 
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【分子编号】41873 【品名】benzhydryl (2E,4E,7R)-11-[(2R,3R)-3-(hydroxymethyl)-4-oxooxetanyl]-3,5,7-trimethyl-2,4-undecadienoate 【CA登记号】 |
【 分 子 式 】C31H38O5 【 分 子 量 】490.63972 【元素组成】C 75.89% H 7.81% O 16.3% |
合成路线1
该中间体在本合成路线中的序号：(XXVII)The Wittig condensation of aldehyde (XIX) with phosphonium salt (XX) by means of KHMDS in THF/toluene gives the vinyloxirane (XXI), which is treated with diiron nonacarbonyl (XXII) in THF to yield the complex (XXIII). Oxidative decomplexation of (XXIII) with CAN in CH3CN gives the vinyl-beta-lactone (XXIV), which is treated with MCPBA and K2CO3 in CH2Cl2 to yield the epoxide (XXV). The ozonolysis of (XXV), followed by reduction with NaBH4 affords the hydroxymethyl-beta-lactone (XXVI), which is deepoxidated with SmI2 in tert-butanol/THF to provide the protected final intermediate (XXVII). Finally this compound is deprotected with TFA/CH2Cl2.
| 【1】 Bates, R.W.; et al.; Total synthesis of the cholesterol biosynthesis inhibitor 1233A via a (Pi-allyl)tricarbonyliron lactone complex. J Chem Soc - Perkins Trans I 1999, 14, 1917. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIX) | 41866 | benzhydryl (2E,4E,7R)-11-[(2R,3R)-3-formyloxiranyl]-3,5,7-trimethyl-2,4-undecadienoate | C30H36O4 | 详情 | 详情 | |
| (XX) | 41867 | (bromomethyl)(triphenyl)phosphorane | 1779-49-3 | C19H18BrP | 详情 | 详情 |
| (XXI) | 41868 | benzhydryl (2E,4E,7R)-3,5,7-trimethyl-11-[(2R,3S)-3-vinyloxiranyl]-2,4-undecadienoate | C31H38O3 | 详情 | 详情 | |
| (XXIII) | 41869 | C33H42O4 | 详情 | 详情 | ||
| (XXIV) | 41870 | benzhydryl (2E,4E,7R)-3,5,7-trimethyl-11-[(2R,3R)-4-oxo-3-vinyloxetanyl]-2,4-undecadienoate | C32H38O4 | 详情 | 详情 | |
| (XXV) | 41871 | benzhydryl (E)-3-(3-methyl-3-[(2R)-2-methyl-6-[(2R,3R)-4-oxo-3-vinyloxetanyl]hexyl]-2-oxiranyl)-2-butenoate | C32H38O5 | 详情 | 详情 | |
| (XXVI) | 41872 | benzhydryl (E)-3-(3-[(2R)-6-[(2R,3R)-3-(hydroxymethyl)-4-oxooxetanyl]-2-methylhexyl]-3-methyl-2-oxiranyl)-2-butenoate | C31H38O6 | 详情 | 详情 | |
| (XXVII) | 41873 | benzhydryl (2E,4E,7R)-11-[(2R,3R)-3-(hydroxymethyl)-4-oxooxetanyl]-3,5,7-trimethyl-2,4-undecadienoate | C31H38O5 | 详情 | 详情 |