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【结 构 式】 
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【药物名称】PNU-96988, U-96988 【化学名称】6-(1-Benzylpropyl)-4-hydroxy-3-(1-phenylpropyl)pyran-2-one 【CA登记号】149394-65-0 【 分 子 式 】C24H26O3 【 分 子 量 】362.47302 |
【开发单位】Pfizer (Originator) 【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY, HIV Protease Inhibitors |
合成路线1
The condensation of 4-hydroxy-6-methyl-2H-pyran-2-one (I) with 1-phenyl-1-propanol (II) by means of TsOH in toluene gives 4-hydroxy-6-methyl-3-(1-phenyl-propyl)-2H-pyran-2-one (III), which is alkylated with benzyl bromide and LDA in THF yielding 4-hydroxy-6-(2-phenylethyl)-3-(1-phenylpropyl)-2H-pyran-2-one (V). Finally this compound is submitted to a new alkylation process with ethyl iodide and LDA in THF to afford the target compound.
| 【1】 Romines, K.R.; Thaisrivongs, S.; Analogs of 4-hydroxypyrone: potent, non-peptidic HIV protease inhibitors. Drugs Fut 1995, 20, 4, 377. |
| 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) | 41231 | 4-hydroxy-6-methyl-2H-pyran-2-one | 675-10-5 | C6H6O3 | 详情 | 详情 |
| (II) | 41232 | 1-phenyl-1-propanol | C9H12O | 详情 | 详情 | |
| (III) | 41233 | 4-hydroxy-6-methyl-3-(1-phenylpropyl)-2H-pyran-2-one | C15H16O3 | 详情 | 详情 | |
| (IV) | 12912 | 1-(Bromomethyl)benzene; Alpha-bromotoluene | 100-39-0 | C7H7Br | 详情 | 详情 |
| (V) | 41234 | 4-hydroxy-6-phenethyl-3-(1-phenylpropyl)-2H-pyran-2-one | C22H22O3 | 详情 | 详情 | |
| (VI) | 10925 | Iodoethane;ethyl iod | 75-03-6 | C2H5I | 详情 | 详情 |
Extended Information