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【结 构 式】 
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【分子编号】10509 【品名】(3R,4S)-1-Benzoyl-3-[[tert-butyl(dimethyl)silyl]oxy]-4-phenyl-2-azetanone 【CA登记号】 |
【 分 子 式 】C22H27NO3Si 【 分 子 量 】381.54682 【元素组成】C 69.26% H 7.13% N 3.67% O 12.58% Si 7.36% |
合成路线1
该中间体在本合成路线中的序号：(IV)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 |