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【结 构 式】 
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【分子编号】54790 【品名】(1S,2S,3R,4S,7R,10S,15S)-4-(acetyloxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11,12-dioxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate 【CA登记号】 |
【 分 子 式 】C29H34O10 【 分 子 量 】542.58296 【元素组成】C 64.2% H 6.32% O 29.49% |
合成路线1
该中间体在本合成路线中的序号：(II)Oxidation of 10-deacetylbaccatin III (I) by means of cupric acetate yielded diketone (II), in equilibrium with the retroaldol product (III). Subsequent reduction employing NaBH4 and CeCl3 produced the seco-taxane (IV) as the major reaction product. Selective protection of the 7 and 9 hydroxyl groups was achieved by treatment with chlorotriethylsilane and imidazole. The resultant 7,9-disilylated derivative (V) was then acylated by the oxazolidinecarboxylic acid (VI) to furnish, after acidic hydrolysis, the title C-seco taxane derivative.
| 【1】 Appendino, G.; et al.; Synthesis and evaluation of C-seco paclitaxel analogues. Tetrahedron Lett 1997, 38, 24, 4273. |
| 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) | 10467 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | 32981-86-5 | C29H36O10 | 详情 | 详情 |
| (II) | 54790 | (1S,2S,3R,4S,7R,10S,15S)-4-(acetyloxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11,12-dioxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate | C29H34O10 | 详情 | 详情 | |
| (III) | 54791 | (1S,2S,3R,9S)-3-[(2R,3S)-3-(acetyloxy)-2-(2-oxoethyl)oxetanyl]-1,5,9-trihydroxy-4,8,11,11-tetramethyl-6-oxobicyclo[5.3.1]undeca-4,7-dien-2-yl benzoate | C29H34O10 | 详情 | 详情 | |
| (IV) | 54792 | (1S,2S,3R,9S)-3-[(2R,3S)-3-(acetyloxy)-2-(2-hydroxyethyl)oxetanyl]-1,5,9-trihydroxy-4,8,11,11-tetramethyl-6-oxobicyclo[5.3.1]undeca-4,7-dien-2-yl benzoate | C29H36O10 | 详情 | 详情 | |
| (V) | 54793 | (1S,2S,3R,9S)-3-((2R,3S)-3-(acetyloxy)-2-{2-[(triethylsilyl)oxy]ethyl}oxetanyl)-1,9-dihydroxy-4,8,11,11-tetramethyl-6-oxo-5-[(triethylsilyl)oxy]bicyclo[5.3.1]undeca-4,7-dien-2-yl benzoate | C41H64O10Si2 | 详情 | 详情 | |
| (VI) | 54794 | (4S,5R)-3-(tert-butoxycarbonyl)-4-isobutyl-2-phenyl-1,3-oxazolidine-5-carboxylic acid | C19H27NO5 | 详情 | 详情 |