• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information