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【结 构 式】 
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【分子编号】56394 【品名】(2R,4R,6S,7R,10R,13S,14R,15S,16S,18S)-13-(acetyloxy)-18-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-(3-fluoro-2-pyridinyl)-2-[(triisopropylsilyl)oxy]propanoyl}oxy)-4-formyl-16-hydroxy-7,19,20,20-tetramethyl-3,5,11-trioxapentacyclo[14.3.1.0~2,6~.0~7,14~.0~10,13~]icosa-1(19),8-dien-15-yl benzoate 【CA登记号】 |
【 分 子 式 】C53H71FN2O14Si 【 分 子 量 】1007.2357232 【元素组成】C 63.2% H 7.1% F 1.89% N 2.78% O 22.24% Si 2.79% |
合成路线1
该中间体在本合成路线中的序号：(IV)Similarly, condensation of taxane (I) with azetidinone (II) in the presence of lithium hexamethyldisilazide affords ester (III). The terminal vinyl group of (III) is converted to aldehyde (IV) by dihydroxylation with NMMO/OsO4, followed by oxidative cleavage with NaIO4. Reductive amination of aldehyde (IV) with dimethylamine and NaBH3CN yields amine (V). Selective catalytic hydrogenation of the disubstituted olefin of (V) produces taxane (VI), which is finally O-desilylated employing tetrabutylammonium fluoride in cold THF.
| 【1】 Soga, T.; Takeda, Y.; Uoto, K. (Daiichi Pharmaceutical Co., Ltd.); Pentacyclic taxane cpds.. EP 1221445; WO 0127115 . |
| 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) | 56392 | (2R,4R,6S,7R,10R,13S,14R,15S,16S,18S)-13-(acetyloxy)-16,18-dihydroxy-7,19,20,20-tetramethyl-4-vinyl-3,5,11-trioxapentacyclo[14.3.1.0~2,6~.0~7,14~.0~10,13~]icosa-1(19),8-dien-15-yl benzoate | C32H38O9 | 详情 | 详情 | |
| (II) | 56387 | tert-butyl (2S,3R)-2-(3-fluoro-2-pyridinyl)-4-oxo-3-[(triisopropylsilyl)oxy]-1-azetidinecarboxylate | C22H35FN2O4Si | 详情 | 详情 | |
| (III) | 56393 | (2R,4R,6S,7R,10R,13S,14R,15S,16S,18S)-13-(acetyloxy)-18-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-(3-fluoro-2-pyridinyl)-2-[(triisopropylsilyl)oxy]propanoyl}oxy)-16-hydroxy-7,19,20,20-tetramethyl-4-vinyl-3,5,11-trioxapentacyclo[14.3.1.0~2,6~.0~7,14~.0~10,13~]icosa-1(19),8-dien-15-yl benzoate | C54H73FN2O13Si | 详情 | 详情 | |
| (IV) | 56394 | (2R,4R,6S,7R,10R,13S,14R,15S,16S,18S)-13-(acetyloxy)-18-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-(3-fluoro-2-pyridinyl)-2-[(triisopropylsilyl)oxy]propanoyl}oxy)-4-formyl-16-hydroxy-7,19,20,20-tetramethyl-3,5,11-trioxapentacyclo[14.3.1.0~2,6~.0~7,14~.0~10,13~]icosa-1(19),8-dien-15-yl benzoate | C53H71FN2O14Si | 详情 | 详情 | |
| (V) | 56395 | (2R,4R,6S,7R,10R,13S,14R,15S,16S,18S)-13-(acetyloxy)-18-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-(3-fluoro-2-pyridinyl)-2-[(triisopropylsilyl)oxy]propanoyl}oxy)-4-[(dimethylamino)methyl]-16-hydroxy-7,19,20,20-tetramethyl-3,5,11-trioxapentacyclo[14.3.1.0~2,6~.0~7,14~.0~10,13~]icosa-1(19),8-dien-15-yl benzoate | C55H78FN3O13Si | 详情 | 详情 | |
| (VI) | 56396 | (2R,4R,6S,7R,10R,13S,14R,15S,16S,18S)-13-(acetyloxy)-18-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-(3-fluoro-2-pyridinyl)-2-[(triisopropylsilyl)oxy]propanoyl}oxy)-4-[(dimethylamino)methyl]-16-hydroxy-7,19,20,20-tetramethyl-3,5,11-trioxapentacyclo[14.3.1.0~2,6~.0~7,14~.0~10,13~]icos-1(19)-en-15-yl benzoate | C55H80FN3O13Si | 详情 | 详情 |