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【结 构 式】 
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【药物名称】 【化学名称】2-Methoxy-5-(3,4,5-trimethoxyphenoxymethyl)phenol 【CA登记号】 【 分 子 式 】C17H20O6 【 分 子 量 】320.34535 |
【开发单位】Paterson Institute Cancer Research (Originator), Univ. Science and Technology Manchester (Originator) 【药理作用】ONCOLYTIC DRUGS, Antimitotic Drugs, Microtubule-Stabilizing Agents |
合成路线1
Isovanillin (I) was protected as the allyl ether (III) by treatment with allyl bromide (II) and K2CO3. Aldehyde reduction of (III) with NaBH4 gave alcohol (IV), which was converted to chloride (V) using SOCl2. Condensation of chloride (V) with the sodium salt of 3,4,5-trimethoxyphenol (VI) produced the corresponding ether (VII). Finally, deprotection of the allyl group of (VII) was achieved by treatment with Wilkinson’s catalyst and DABCO.
| 【1】 McGown, A.T.; Hadfield, J.A.; Rennison, D.; Woo, M.; Lawrence, N.J.; Antimitotic and cell growth inhibitory properties of combrestastatin A-4-like ethers. Bioorg Med Chem Lett 2001, 11, 1, 51. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 18455 | 3-hydroxy-4-methoxybenzaldehyde; Isovanillin | 621-59-0 | C8H8O3 | 详情 | 详情 |
| (II) | 11463 | 3-Bromo-1-propene; 3-Bromopropene；allyl bromide | 106-95-6 | C3H5Br | 详情 | 详情 |
| (III) | 48348 | 3-Allyloxy-4-methoxybenzaldehyde | C11H12O3 | 详情 | 详情 | |
| (IV) | 48349 | [3-(allyloxy)-4-methoxyphenyl]methanol | C11H14O3 | 详情 | 详情 | |
| (V) | 48350 | allyl 5-(chloromethyl)-2-methoxyphenyl ether; 2-(allyloxy)-4-(chloromethyl)-1-methoxybenzene | C11H13ClO2 | 详情 | 详情 | |
| (VI) | 37163 | 3,4,5-trimethoxyphenol | C9H12O4 | 详情 | 详情 | |
| (VII) | 48351 | allyl 2-methoxy-5-[(3,4,5-trimethoxyphenoxy)methyl]phenyl ether; 5-[[3-(allyloxy)-4-methoxybenzyl]oxy]-1,2,3-trimethoxybenzene | C20H24O6 | 详情 | 详情 |
Extended Information