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【结 构 式】 
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【分子编号】38774 【品名】2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadec-10-yl]-1-ethanol 【CA登记号】 |
【 分 子 式 】C17H28O5 【 分 子 量 】312.40632 【元素组成】C 65.36% H 9.03% O 25.61% |
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：(III)Coupling of dihydroartemisinin (I) with allyl trimethylsilane in the presence of boron trifluoride etherate gave the 10beta-allyl deoxo derivative (II). Subsequent ozonization of the allyl double bond of (II), followed by reductive treatment with NaBH4, provided alcohol (III). Finally, alkylation of (III) with 2-fluorobenzyl bromide (IV) in the presence of NaH furnished the corresponding 2-fluorobenzyl ether.
| 【1】 Searle, N.L.; Maggs, J.L.; Kan, K.-W.; Ward, S.A.; O'Neill, P.M.; Raynes, K.; Park, K.; Storr, R.C.; Novel, potent, semisynthetic antimalarial carba analogues of the first-generation 1,2,4-trioxane artemether. J Med Chem 1999, 42, 26, 5487. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 15775 | Allyltrimethylsilane; allyl(trimethyl)silane | 762-72-1 | C6H14Si | 详情 | 详情 | |
| (I) | 22370 | Dihydroartemisinin; (1R,4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecan-10-ol | C15H24O5 | 详情 | 详情 | |
| (II) | 38773 | (1R,4S,5R,8S,9R,10R,12R,13R)-10-allyl-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecane | C18H28O4 | 详情 | 详情 | |
| (III) | 38774 | 2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadec-10-yl]-1-ethanol | C17H28O5 | 详情 | 详情 | |
| (IV) | 38775 | 1-(bromomethyl)-2-fluorobenzene | 446-48-0 | C7H6BrF | 详情 | 详情 |
Extended Information