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【结 构 式】 
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【分子编号】54904 【品名】(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-azido-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 【CA登记号】 |
【 分 子 式 】C40H45N3O13 【 分 子 量 】775.80972 【元素组成】C 61.93% H 5.85% N 5.42% O 26.81% |
合成路线1
该中间体在本合成路线中的序号：(V)The reaction of baccatine III (I) with trichloroacetyl chloride in pyridine gives 7-O-(trichloroacetyl)baccatine III (II), which is condensed with 2,3-epoxy-3-phenylpropionic acid (III) by means of DCC and DMAP in toluene to yield the ester (IV). Opening of the epoxide ring of (IV) by means of sodium azide and methyl formate in methanol affords the expected hydroxy azide (V), which is reduced with PPh3 in dichloromethane/water to provide the corresponding amino derivative (VI). Finally, the amino group of (VI) is benzoylated with benzoyl chloride (VII) and NaHCO3 in ethyl acetate/water to furnish the target paclitaxel.
| 【1】 Bombardelli, E.; Pontiroli, A.; Battaglia, A.; Dambruoso, P.; Guerrini, A. (Indena SpA); A process for the preparation of paclitaxel. WO 0246177 . |
| 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) | 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) | 38901 | (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-trichloroacetyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C33H37Cl3O12 | 详情 | 详情 | |
| (III) | 23891 | (2R,3R)-3-phenyl-2-oxiranecarboxylic acid | C9H8O3 | 详情 | 详情 | |
| (IV) | 54903 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(2,2,2-trichloroacetyl)oxy]-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-15-yl (2R,3R)-3-phenyl-2-oxiranecarboxylate | C42H43Cl3O14 | 详情 | 详情 | |
| (V) | 54904 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-azido-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 | C40H45N3O13 | 详情 | 详情 | |
| (VI) | 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 | |
| (VII) | 10463 | Benzoyl chloride | 98-88-4 | C7H5ClO | 详情 | 详情 |