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【结 构 式】

【分子编号】10506

【品名】1-[[(dicyclohexylamino)sulfonyl]methyl]-7,7-dimethylbicyclo[2.2.1]hept-2-yl 2-[[tert-butyl(dimethyl)silyl]oxy]acetate

【CA登记号】

【 分 子 式 】C30H55NO5SSi

【 分 子 量 】569.92194

【元素组成】C 63.22% H 9.73% N 2.46% O 14.04% S 5.63% Si 4.93%

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:(I)

A new synthesis of paclitaxel starting from baccatin III has been described: The cyclocondensation of the Oppolzer's chiral auxiliary esterified with silylated glycolic acid (I) with benzaldehyde trimethylsilylimine (II) by means of lithium diisopropylamide (LDA) in THF gives (3R,4S)-3-(tert-butyldimethylsilyloxy)-4-phenylazetidin-2-one (III), which is benzoylated with benzoyl chloride and triethylamine/dimethylaminopyridine (DMAP) in dichloromethane, yielding (3R,4S)-1-benzoyl-3-(tert-butyldimethylsilyloxy)-4-phenylazetidin-2-one (IV). The condensation of (IV) with 7-O-(triethylsilyl)baccatin III (V) by means of NaH in THF affords silylated paclitaxel (VI), which is finally deprotected with HF in pyridine.

1 Hepperle, M.; Park, H.; Georg, G.I.; Cheruvallath, Z.S.; Harriman, G.C.B.; An efficient semisynthesis of taxol from (3R,4S)-N-benzoyl-3-[(t-butyldimethylsilyl)oxy]-4-phenyl-2-azetidinone and 7-(triethylsilyl)baccatin III. Bioorg Med Chem Lett 1993, 3, 11, 2467.
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) 10506 1-[[(dicyclohexylamino)sulfonyl]methyl]-7,7-dimethylbicyclo[2.2.1]hept-2-yl 2-[[tert-butyl(dimethyl)silyl]oxy]acetate C30H55NO5SSi 详情 详情
(II) 10507 Trimethyl-N-[(E)-benzylidene]silanamine; N-[(E)-Benzylidene]-N-(trimethylsilyl)amine 17599-61-0 C10H15NSi 详情 详情
(III) 10508 (3R,4S)-3-[[Tert-butyl(dimethyl)silyl]oxy]-4-phenyl-2-azetanone C15H23NO2Si 详情 详情
(IV) 10509 (3R,4S)-1-Benzoyl-3-[[tert-butyl(dimethyl)silyl]oxy]-4-phenyl-2-azetanone C22H27NO3Si 详情 详情
(V) 10473 (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
(VI) 10511 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[((2R,3S)-3-(benzoylamino)-2-[[tert-butyl(dimethyl)silyl]oxy]-3-phenylpropanoyl)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
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