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【结 构 式】 
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【分子编号】10735 【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-([(2R,3S)-3-[[(E)-2-oxopropylidene]amino]-3-phenyl-2-[(triethylsilyl)oxy]propanoyl]oxy)-9-[(triethylsilyl)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 】C55H77NO14Si2 【 分 子 量 】1032.38572 【元素组成】C 63.99% H 7.52% N 1.36% O 21.7% Si 5.44% |
合成路线1
该中间体在本合成路线中的序号：(X)2) The silylation of Taxol B (VI) with triethylsilyl chloride as before gives the bis(triethylsilyl) compound (VII), which by reduction with zirconocene chloride hydride as described yields compound (VIII). Finally, the hydrolytic cleavage of (VIII) with simultaneous desilylation with HCl in ethanol affords the previously reported compound (IV) with its free amino group easily benzoylated to Taxol. 3) The ozonolysis of the silylated Taxol B (VII) with O3 in methanol gives compound (IX), which is reduced with zirconocene as before yielding the 2-oxopropylideneimine (X). Finally, the hydrolytic cleavage of (X) with simultaneous desilylation with HCl in ethanol affords the previously reported compound (IX) with its free amino group easiely benzoylated to Taxol.
| 【1】 Young, T.H. (Hauser, Inc.); Preparation of Taxol and docetaxel through primary amines. EP 0852581; WO 9623780 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 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 | |
| (VI) | 10731 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,9-dihydroxy-15-[((2R,3S)-2-hydroxy-3-[[(E)-2-methyl-2-butenoyl]amino]-3-phenylpropanoyl)oxy]-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C45H53NO14 | 详情 | 详情 | |
| (VII) | 10732 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1-hydroxy-10,14,17,17-tetramethyl-15-([(2R,3S)-3-[[(E)-2-methyl-2-butenoyl]amino]-3-phenyl-2-[(triethylsilyl)oxy]propanoyl]oxy)-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C57H81NO14Si2 | 详情 | 详情 | |
| (VIII) | 10733 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,9-dihydroxy-15-[((2R,3S)-2-hydroxy-3-[[(E,2E)-2-methyl-2-butenylidene]amino]-3-phenylpropanoyl)oxy]-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C45H53NO13 | 详情 | 详情 | |
| (IX) | 10734 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-15-([(2R,3S)-3-phenyl-3-(pyruvoylamino)-2-[(triethylsilyl)oxy]propanoyl]oxy)-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C55H77NO15Si2 | 详情 | 详情 | |
| (X) | 10735 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-15-([(2R,3S)-3-[[(E)-2-oxopropylidene]amino]-3-phenyl-2-[(triethylsilyl)oxy]propanoyl]oxy)-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C55H77NO14Si2 | 详情 | 详情 |