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【结 构 式】 
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【分子编号】10489 【品名】(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-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 】C31H37O11T 【 分 子 量 】588.64504 【元素组成】C 63.25% H 6.34% O 29.9% T 0.51% |
合成路线1
该中间体在本合成路线中的序号：(XVII)The synthesis of tritium-labeled taxol [13-3H]-taxol (b) has been described: The oxidation of baccatin III (I) with MnO2 in chloroform gives 13-oxobaccatin III (XV), which is silylated with chlorotriethylsilane in pyridine yielding 13-oxo-7-O-(triethylsilyl)baccatin III (XVI). The reduction of (XVI) with tritiated borane (prepared from tritiated sodium borohydride and BF3) in THF affords [13-3H]-7-O-(triethylsilyl)baccatin III (XVII), which is condensed with (3S-cis)-1-benzoyl-4-phenyl-3-(trimethylsilyloxy)azetidin-2-one (XVIII) by means of butyllithium in THF to give [13-3H]-2',7-bis-O-(triethylsilyl)taxol (XIX). Finally, this compound is deprotected with 48% HF and pyridine in THF.
| 【1】 Taylor, G.F.; Thornton, S.S.; Tallent, C.R.; Kepler, J.A.; Synthesis of [3''-3H]taxol and [13-3H]taxol. J Label Compd Radiopharm 1993, 33, 6, 501. |
| 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 | |
| (XV) | 10487 | (1S,2S,3R,4S,7R,9S,10S,12R)-4,12-bis(acetoxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11,15-dioxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C31H36O11 | 详情 | 详情 | |
| (XVI) | 10488 | (1S,2S,3R,4S,7R,9S,10S,12R)-4,12-bis(acetoxy)-1-hydroxy-10,14,17,17-tetramethyl-11,15-dioxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C37H50O11Si | 详情 | 详情 | |
| (XVII) | 10489 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C31H37O11T | 详情 | 详情 | |
| (XVII) | 44661 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C37H52O11Si | 详情 | 详情 | |
| (XVIII) | 10490 | (3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-2-azetanone | C22H27NO3Si | 详情 | 详情 | |
| (XIX) | 10491 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-([(2R,3S)-3-(benzoylamino)-3-phenyl-2-[(triethylsilyl)oxy]propanoyl]oxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C59H79NO14Si2 | 详情 | 详情 | |
| (XIX) | 44662 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-([(2R,3S)-3-(benzoylamino)-3-phenyl-2-[(triethylsilyl)oxy]propanoyl]oxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl | C59H79NO14Si2 | 详情 | 详情 |