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【结 构 式】 
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【药物名称】XR-3054 【化学名称】cis-8-Isopropenyl-2,2-dimethyl-1,3-dioxaspiro[4.5]decane 【CA登记号】 【 分 子 式 】C13H22O2 【 分 子 量 】210.31909 |
【开发单位】Xenova (Originator) 【药理作用】Chemopreventive Agents, Oncolytic Drugs, Farnesyl Transferase Inhibitors, Inhibitors of Signal Transduction Pathways |
合成路线1
Sharpless asymmetric epoxidation of (S)-(-)-perillyl alcohol (I) using tert-butyl hydroperoxide and diethyl L-tartrate produced epoxide (II), which was reduced to diol (III) by means of LiAlH4 in cold THF. Treatment of (III) with 2,2-dimethoxypropane (IV) and p-toluenesulfonic acid then furnished the title isopropylidene ketal.
| 【1】 Ryder, H.; Skoumas, V.; Watson, M.; Moore, M.; Coombes, R.C.; Ashworth, P.A.; Donaldson, M.J.; XR 3054, structurally related to limonene, is a novel inhibitor of farnesyl protein transferase. Eur J Cancer 1999, 35, 6, 1014. |
| 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) | 34756 | [(4S)-4-isopropenyl-1-cyclohexen-1-yl]methanol | 536-59-4 | C10H16O | 详情 | 详情 |
| (II) | 34757 | [(4S,6S)-4-isopropenyl-7-oxabicyclo[4.1.0]hept-1-yl]methanol | C10H16O2 | 详情 | 详情 | |
| (III) | 34758 | 1-(hydroxymethyl)-4-isopropenylcyclohexanol | C10H18O2 | 详情 | 详情 | |
| (IV) | 10722 | 1-Methoxy-1-methylethyl methyl ether; 2,2-Dimethoxypropane | 77-76-9 | C5H12O2 | 详情 | 详情 |
Extended Information