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【结 构 式】 
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【分子编号】27944 【品名】1-[4-(2-hydroxyethoxy)-3-iodo-5-methoxyphenyl]-4-(3,4,5-trimethoxyphenyl)-1,4-butanediol 【CA登记号】 |
【 分 子 式 】C22H29IO8 【 分 子 量 】548.37193 【元素组成】C 48.19% H 5.33% I 23.14% O 23.34% |
合成路线1
该中间体在本合成路线中的序号：(VI)Alkylation of 5-iodovanillin (I) with iodoethanol gave hydroxyethyl ether (II). This was condensed with vinyl ketone (III) in the presence of the thiazolium salt (IV) to produce the 1,4-diketone (V). Subsequent reduction of (V) with NaBH4 afforded 1,4-diol (VI), which was cyclized with trifluoroacetic acid in chloroform to furnish a mixture of cis and trans diaryltetrahydrofurans. The required trans isomer (VII) was isolated by column chromatography, and then treated with methanesulfonyl chloride and triethylamine to give mesylate (VIII). Further condensation of (VIII) with 4-chlorothiophenol (IX) provided sulfide (X). Finally, displacement of the iodine atom with CuCN in boiling DMF produced the title nitrile.
| 【1】 Cai, X.; et al.; (+-)-trans-2-[3-Methoxy-4-(4-chlorophenylthioethoxy)-5-(N-methyl-N-hydroxyureidyl)methylphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (CMI-392), a potent dual 5-lipoxygenase inhibitor and platelet-activating factor receptor antagonist. J Med Chem 1998, 41, 11, 1970. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 38258 | 2-iodo-1-ethanol | 624-76-0 | C2H5IO | 详情 | 详情 | |
| (I) | 12758 | 4-Hydroxy-3-iodo-5-methoxybenzaldehyde; 5-Iodovanillin | 5438-36-8 | C8H7IO3 | 详情 | 详情 |
| (II) | 27940 | 4-(2-hydroxyethoxy)-3-iodo-5-methoxybenzaldehyde | C10H11IO4 | 详情 | 详情 | |
| (III) | 27941 | 1-(3,4,5-trimethoxyphenyl)-2-propen-1-one | C12H14O4 | 详情 | 详情 | |
| (IV) | 27942 | 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride | 4568-71-2 | C13H16ClNOS | 详情 | 详情 |
| (V) | 27943 | 1-[4-(2-hydroxyethoxy)-3-iodo-5-methoxyphenyl]-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione | C22H25IO8 | 详情 | 详情 | |
| (VI) | 27944 | 1-[4-(2-hydroxyethoxy)-3-iodo-5-methoxyphenyl]-4-(3,4,5-trimethoxyphenyl)-1,4-butanediol | C22H29IO8 | 详情 | 详情 | |
| (VII) | 27945 | 2-[2-iodo-6-methoxy-4-[(2S,5S)-5-(3,4,5-trimethoxyphenyl)tetrahydro-2-furanyl]phenoxy]-1-ethanol | C22H27IO7 | 详情 | 详情 | |
| (VIII) | 27946 | 2-[2-iodo-6-methoxy-4-[(2S,5S)-5-(3,4,5-trimethoxyphenyl)tetrahydro-2-furanyl]phenoxy]ethyl methanesulfonate | C23H29IO9S | 详情 | 详情 | |
| (IX) | 27947 | 4-chlorobenzenethiol | 106-54-7 | C6H5ClS | 详情 | 详情 |
| (X) | 27948 | (2S,5S)-2-(4-[2-[(4-chlorophenyl)sulfanyl]ethoxy]-3-iodo-5-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran | C28H30ClIO6S | 详情 | 详情 |