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【结 构 式】 
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【分子编号】39172 【品名】methyl (2E,5Z)-7-[(1R,2S,3R,5S)-5-hydroxy-2-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-butenyl]-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-2,5-heptadienoate 【CA登记号】 |
【 分 子 式 】C30H39F3O7 【 分 子 量 】568.6306696 【元素组成】C 63.37% H 6.91% F 10.02% O 19.7% |
合成路线1
该中间体在本合成路线中的序号：(VII)The Wittig reaction of 1alpha-acetoxy-2alpha-(6-methoxycarbonyl-hex-2-cis-enyl)-3beta-formyl-4alpha-(2-tetrahydropyranyloxy)cyclopentane (I) and dimethyl 2-oxo-3-(3-trifluoromethylphenoxy)propylphosphonate (II) by means of NaH in hot THF gives 9alpha-acetoxy-11alpha-(2-tetrahydropyranyloxy)-15-oxo-16-(3-trifluoromethylphenoxy)-17,18,19,20-tetranorprosta-5-cis-13-trans-dienoate (III), which is reduced with NaBH4 in methanol yielding the protected trihydroxy compound (IV). The partial hydrolysis of (IV) with K2CO3 in methanol affords the dihydroxytetrahydropyranyloxy compound (V), which by reaction with diphenyldiselenide (A) by means of 17-butyllithium and diisopropylamine in THF is converted into the mixed selenide (VI). The treatment of (VI) with H2O2 in THF-ethyl acetate gives methyl 9alpha,15alpha-dihydroxy-11alpha-(2-tetra)-17,18,19,20-tetranorprosta-2-trans-5-cis-13-trans-trienoate (VII), which is finally treated with HCl in THF-water to eliminate the tetrahydropyranyl group.
| 【1】 Hayashi, M.; et al.; US 4065632 . |
| 【2】 Castaner, J.; Riberos, J.; ONO-995. Drugs Fut 1980, 5, 10, 499. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 39170 | 1,2-diphenyldiselane | 1666-13-3 | C12H10Se2 | 详情 | 详情 |
| (I) | 20983 | methyl (Z)-7-[(1R,2S,3R,5S)-5-(acetoxy)-2-formyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoate | C22H34O7 | 详情 | 详情 | |
| (II) | 32121 | dimethyl 2-oxo-3-[3-(trifluoromethyl)phenoxy]propylphosphonate | C12H14F3O5P | 详情 | 详情 | |
| (III) | 39167 | methyl (Z)-7-[(1R,2S,3R,5S)-5-(acetoxy)-2-[(E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-butenyl]-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoate | C32H41F3O8 | 详情 | 详情 | |
| (IV) | 39168 | methyl (Z)-7-[(1R,2S,3R,5S)-5-(acetoxy)-2-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-butenyl]-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoate | C32H43F3O8 | 详情 | 详情 | |
| (V) | 39169 | methyl (Z)-7-[(1R,2S,3R,5S)-5-hydroxy-2-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-butenyl]-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoate | C30H41F3O7 | 详情 | 详情 | |
| (VI) | 39171 | methyl (Z)-7-[(1R,2S,3R,5S)-5-hydroxy-2-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-butenyl]-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-2-(phenylselanyl)-5-heptenoate | C36H45F3O7Se | 详情 | 详情 | |
| (VII) | 39172 | methyl (2E,5Z)-7-[(1R,2S,3R,5S)-5-hydroxy-2-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-butenyl]-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-2,5-heptadienoate | C30H39F3O7 | 详情 | 详情 |