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【结 构 式】 
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【分子编号】56876 【品名】(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-({(2R,3S)-3-{[(benzyloxy)carbonyl]amino}-2-[(benzyloxy)methoxy]-3-phenylpropanoyl}oxy)-9-{[(benzyloxy)carbonyl]oxy}-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate 【CA登记号】 |
【 分 子 式 】C64H67NO18 【 分 子 量 】1138.23192 【元素组成】C 67.53% H 5.93% N 1.23% O 25.3% |
合成路线1
该中间体在本合成路线中的序号：(I)The hydrogenation of the protected taxol derivative (I) with H2 over Pd/C in aqueous THF in the presence of HCl gives the 3'-amino-taxol derivative (II), which is N-benzoylated by means of benzoyl chloride (III) and TEA to provide the target paclitaxel.
| 【1】 McChesney, J.D.; Zygmunt, J. (NaPro BioTherapeutics, Inc.); Two-step conversion of protected taxane ester to paclitaxel. WO 0285878 . |
| 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) | 56876 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-({(2R,3S)-3-{[(benzyloxy)carbonyl]amino}-2-[(benzyloxy)methoxy]-3-phenylpropanoyl}oxy)-9-{[(benzyloxy)carbonyl]oxy}-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate | C64H67NO18 | 详情 | 详情 | |
| (II) | 10729 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy]-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C40H47NO13 | 详情 | 详情 | |
| (III) | 10463 | Benzoyl chloride | 98-88-4 | C7H5ClO | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)The hydrogenation of the protected taxol derivative (I) with H2 over Pd/C in aqueous THF gives the 3'-amino-2'-O-Bom protected taxol derivative (II), which is N-benzoylated by means of benzoyl anhydride (III) to provide the 2'-O-Bom protected taxol (IV). Finally this compound is deprotected by hydrogenation with H2 over Pd/C in THF/water in the presence of HCl or H2SO4 to afford the target paclitaxel.
| 【1】 McChesney, J.D.; Zygmunt, J. (NaPro BioTherapeutics, Inc.); Three-step conversion of protected taxane ester to paclitaxel. WO 0285879 . |
| 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) | 56876 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-({(2R,3S)-3-{[(benzyloxy)carbonyl]amino}-2-[(benzyloxy)methoxy]-3-phenylpropanoyl}oxy)-9-{[(benzyloxy)carbonyl]oxy}-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate | C64H67NO18 | 详情 | 详情 | |
| (II) | 56877 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-({(2R,3S)-3-amino-2-[(benzyloxy)methoxy]-3-phenylpropanoyl}oxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate | C48H55NO14 | 详情 | 详情 | |
| (III) | 56878 | 1-phenylvinyl benzoate | C15H12O2 | 详情 | 详情 | |
| (IV) | 10747 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-([(2R,3S)-3-(benzoylamino)-2-[(benzyloxy)methoxy]-3-phenylpropanoyl]oxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C55H59NO15 | 详情 | 详情 |