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【结 构 式】 
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【分子编号】13846 【品名】methyl 5-[(3aS,5R,6S,6aS)-6-((E,3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-1-octenyl)-5-hydroxy-1,3a,4,5,6,6a-hexahydro-2-pentalenyl]pentanoate 【CA登记号】 |
【 分 子 式 】C28H50O4Si 【 分 子 量 】478.7881 【元素组成】C 70.24% H 10.53% O 13.37% Si 5.87% |
合成路线1
该中间体在本合成路线中的序号：(CXX), (CXIX)15) The synthesis of the 11beta-tritiated clinprost can be performed as follows: The disilylated compound (XCIII), already reported in Scheme 7, is carefully treated with TBAF in THF and the resulting mixture of 11- and 15-monosilylated compounds is separated by column chromatography over silicagel in hexane/ethylacetate giving the 15-O-silylated compound (CXX), which is oxidized with CrO3/Pyr in dichloromethane yielding the ketonic compound (CXXI). The reduction of (CXXI) with NaB3H4 and CeCl3 in diglyme affords the 11-tritiated compound (CXXII) as an epimeric mixture on the 11-carbon, which was resolved by column chromatography giving enantiomerically pure (CXXII). Finally, this compound is desilylated with TBAF as usual.
| 【1】 Graul, A.; Leeson, P.; Castaner, J.; Clinprost. Drugs Fut 1997, 22, 6, 608. |
| 【2】 Sugiura, S.; Kurozumi, S.; Ikegami, S.; Synthesis of tritium-labelled isocarbacyclin derivatives, radiolabelled prostaglandin I1 analogs (1). J Label Compd Radiopharm 1995, 38, 2, 129-38. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (CXX), (CXIX) | 13846 | methyl 5-[(3aS,5R,6S,6aS)-6-((E,3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-1-octenyl)-5-hydroxy-1,3a,4,5,6,6a-hexahydro-2-pentalenyl]pentanoate | C28H50O4Si | 详情 | 详情 | |
| (CXXI) | 13847 | methyl 5-[(3aS,6S,6aS)-6-((E,3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-1-octenyl)-5-oxo-1,3a,4,5,6,6a-hexahydro-2-pentalenyl]pentanoate | C28H48O4Si | 详情 | 详情 | |
| (CXIX) | 63807 | methyl 5-[6-(3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-octenyl)-5-hydroxy-1,3a,4,5,6,6a-hexahydro-2-pentalenyl]pentanoate | C28H50O4Si | 详情 | 详情 | |
| (XCIII) | 13817 | methyl 5-[(3aS,5R,6S,6aS)-5-[[tert-butyl(dimethyl)silyl]oxy]-6-((E,3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-1-octenyl)-1,3a,4,5,6,6a-hexahydro-2-pentalenyl]pentanoate | C34H64O4Si2 | 详情 | 详情 |