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【结 构 式】 
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【分子编号】10450 【品名】(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-15-[[(Z)-3-phenyl-2-propenoyl]oxy]-9-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 【CA登记号】 |
【 分 子 式 】C43H45Cl3O14 【 分 子 量 】892.18 【元素组成】C 57.89% H 5.08% Cl 11.92% O 25.11% |
合成路线1
该中间体在本合成路线中的序号：(IV)A process for the preparation of taxol has been described: The acylation of baccatin III (I) with 2,2,2-trichloroethyl chloroformate in pyridine yields the chloroformate (II), which is acylated with cinnamic acid (III) by means of oxalyl chloride of dicyclohexylcarbodiimide to the cinnamate (IV). The oxidative addition of tert-butyl N-chlorocarbamate (V) to (IV) by means of OsO4 in water affords the protected amino hydroxyester (VI), which is deprotected with iodotrimethylsilane in acetonitrile to give the free aminoester (VII). The benzoylation of (VII) with benzoyl chloride in pyridine affords the protected N-benzoyl derivative (VIII), which is finally deprotected by treatment with Zn and acetic acid to eliminate the trichloroethoxycarbonyl group.
| 【1】 Colin, M.; Guenard, D.; Gueritte-Voegelein, F.; Potier, P. (Aventis SA); Process for the preparation of taxol and 10-deacetyltaxol. US 4857653 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10463 | Benzoyl chloride | 98-88-4 | C7H5ClO | 详情 | 详情 | |
| (I) | 10447 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C31H38O11 | 详情 | 详情 | |
| (II) | 10448 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C34H39Cl3O13 | 详情 | 详情 | |
| (III) | 10449 | (Z)-3-Phenyl-2-propenoic acid | 621-82-9 | C9H8O2 | 详情 | 详情 |
| (IV) | 10450 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-15-[[(Z)-3-phenyl-2-propenoyl]oxy]-9-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C43H45Cl3O14 | 详情 | 详情 | |
| (VI) | 10451 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-([3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C48H56Cl3NO17 | 详情 | 详情 | |
| (VII) | 10452 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[(3-amino-2-hydroxy-3-phenylpropanoyl)oxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C43H48Cl3NO15 | 详情 | 详情 | |
| (VIII) | 10453 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C50H52Cl3NO16 | 详情 | 详情 |