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【结 构 式】 
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【分子编号】51264 【品名】benzyl (2R,3S)-2-allyl-3-(benzyloxy)-1-piperidinecarboxylate 【CA登记号】 |
【 分 子 式 】C23H27NO3 【 分 子 量 】365.47232 【元素组成】C 75.59% H 7.45% N 3.83% O 13.13% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(XXII)The desulfurization of (XXI) with H2O2 and CaCO3 gives the chiral allylpiperidine (XXII), which is epoxidized by oxidation with OsO4, reaction of Ts-OH and treatment with K2CO3 to yield the epoxide (XXIII). The condensation of (XXIII) with quinazolinone (XXIV) by means of KOH in methanol affords the substituted propanol (XXV), which is oxidized with DMP to provide the propanone derivative (XXVI). Finally, compound (XXVI) is deprotected by treatment with refluxing 6N HCl to give the target febrifugine.
| 【1】 Taniguchi, T.; Ofasawara, K.; A diastereocontrolled synthesis of (+)-febrifugine: A potent antimalarial piperidine alkaloid. Org Lett 2000, 2, 20, 3193. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXI) | 50262 | 3-hydroxypropyl methanesulfonate | C4H10O4S | 详情 | 详情 | |
| (XXII) | 51264 | benzyl (2R,3S)-2-allyl-3-(benzyloxy)-1-piperidinecarboxylate | C23H27NO3 | 详情 | 详情 | |
| (XXIII) | 51265 | benzyl (2R,3S)-3-(benzyloxy)-2-(2-oxiranylmethyl)-1-piperidinecarboxylate | C23H27NO4 | 详情 | 详情 | |
| (XXIV) | 14634 | 4(3H)-quinazolinone | C8H6N2O | 详情 | 详情 | |
| (XXV) | 51266 | benzyl (2R,3S)-3-(benzyloxy)-2-[2-hydroxy-3-[4-oxo-3(4H)-quinazolinyl]propyl]-1-piperidinecarboxylate | C31H33N3O5 | 详情 | 详情 | |
| (XXVI) | 51267 | benzyl (2R,3S)-3-(benzyloxy)-2-[2-oxo-3-[4-oxo-3(4H)-quinazolinyl]propyl]-1-piperidinecarboxylate | C31H31N3O5 | 详情 | 详情 |
Extended Information