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【结 构 式】 
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【分子编号】56088 【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-(4-{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]acetyl}phenyl)-1-ethanone 【CA登记号】 |
【 分 子 式 】C40H54O10 【 分 子 量 】694.86276 【元素组成】C 69.14% H 7.83% O 23.03% |
合成路线1
该中间体在本合成路线中的序号：(VIa)Reduction of artemisinin (I) with NaBH4 at low temperature provided dihydroartemisinin (II), which was subsequently converted to the alpha-acetate (III) upon treatment with acetyl chloride in pyridine. The bis(trimethylsilyl) enol ether (V) - prepared by silylation of 1,4-diacetylbenzene (IV) with trimethylsilyl triflate - was then coupled to dihydroartemisinin acetate (III) in the presence of SnCl4 at -78 C to produce a diastereoisomeric mixture of adducts (VIa-c). The title alpha,alpha-dimer was then isolated as a minor component by means of preparative HPLC.
| 【1】 Borstnik, K.; Posner, G.H.; Paik, I.-H.; Dolan, P.; Kensler, T.W.; Xie, S.; Shapiro, T.A.; Northrop, J.; New chemical and biological aspects of artemisinin-derived trioxane dimers. Bioorg Med Chem 2002, 10, 1, 227. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIa) | 56088 | 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-(4-{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]acetyl}phenyl)-1-ethanone | C40H54O10 | 详情 | 详情 | |
| (VIb) | 56089 | 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-(4-{2-[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadec-10-yl]acetyl}phenyl)-1-ethanone | C40H54O10 | 详情 | 详情 | |
| (VIc) | 56090 | 2-[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadec-10-yl]-1-(4-{2-[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadec-10-yl]acetyl}phenyl)-1-ethanone | C40H54O10 | 详情 | 详情 | |
| (I) | 22369 | Qinghaosu; Artemisine; (1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecan-10-one | 63968-64-9 | C15H22O5 | 详情 | 详情 |
| (II) | 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 | |
| (III) | 56087 | (1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadec-10-yl acetate | C17H26O6 | 详情 | 详情 | |
| (IV) | 42273 | 1-(4-acetylphenyl)-1-ethanone | 1009-61-6 | C10H10O2 | 详情 | 详情 |
| (V) | 42274 | trimethylsilyl 1-(4-[1-[(trimethylsilyl)oxy]vinyl]phenyl)vinyl ether; trimethyl[[1-(4-[1-[(trimethylsilyl)oxy]vinyl]phenyl)vinyl]oxy]silane | C16H26O2Si2 | 详情 | 详情 |