【结 构 式】 |
【分子编号】49347 【品名】(1S,2S,3R,4S,7R,9S,11R,13R,16S)-4,13-bis(acetoxy)-16-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-phenyl-2-[(triethylsilyl)oxy]propanoyl]oxy)-1-hydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.0(3,11).0(4,7).0(9,11)]octadec-14-en-2-yl benzoate 【CA登记号】 |
【 分 子 式 】C51H67NO14Si 【 分 子 量 】946.17682 【元素组成】C 64.74% H 7.14% N 1.48% O 23.67% Si 2.97% |
合成路线1
该中间体在本合成路线中的序号:(VII)The reaction of taxol (I) with benzyloxycarbonyl chloride and DIEA in dichloromethane gives the protected compound (II), which is treated with DAST in the same solvent to yield the cyclopropa taxol (III). The hydrogenolysis of (III) with H2 over Pd/C affords compound (IV), which is deacylated with tetrabutylammonium borohydride in dichloromethane to provide the cyclopropa baccatin (V). The acylation of (V) with azetidinone (VI) by means of BuLi in THF gives the silylated taxoid (VII), which is finally desilylated with HCl in acetonitrile to afford the target compound.
【1】 Chen, S.-H.; Farina, V. (Bristol-Myers Squibb Co.); 7,8-Cyclopropataxones. CA 2099211; EP 0577083; JP 1994179665; JP 1994179666; JP 2001199974; US 5254580 . |
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) | 10595 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-(benzoylamino)-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 | 33069-62-4 | C47H51NO14 | 详情 | 详情 |
(II) | 49342 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[((2R,3S)-3-(benzoylamino)-2-[[(benzyloxy)carbonyl]oxy]-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 | C55H57NO16 | 详情 | 详情 | |
(III) | 49343 | (1S,2S,3R,4S,7R,9S,11R,13R,16S)-4,13-bis(acetoxy)-16-[((2R,3S)-3-(benzoylamino)-2-[[(benzyloxy)carbonyl]oxy]-3-phenylpropanoyl)oxy]-1-hydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.0(3,11).0(4,7).0(9,11)]octadec-14-en-2-yl benzoate | C55H55NO15 | 详情 | 详情 | |
(IV) | 49344 | (1S,2S,3R,4S,7R,9S,11R,13R,16S)-4,13-bis(acetoxy)-16-[[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy]-1-hydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.0(3,11).0(4,7).0(9,11)]octadec-14-en-2-yl benzoate | C47H49NO13 | 详情 | 详情 | |
(V) | 49345 | (1S,2S,3R,4S,7R,9S,11R,13R,16S)-4,13-bis(acetoxy)-1,16-dihydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.0(3,11).0(4,7).0(9,11)]octadec-14-en-2-yl benzoate | C31H36O10 | 详情 | 详情 | |
(VI) | 49346 | tert-butyl (3R,4S)-2-oxo-4-phenyl-3-[(triethylsilyl)oxy]-1-azetidinecarboxylate | C20H31NO4Si | 详情 | 详情 | |
(VII) | 49347 | (1S,2S,3R,4S,7R,9S,11R,13R,16S)-4,13-bis(acetoxy)-16-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-phenyl-2-[(triethylsilyl)oxy]propanoyl]oxy)-1-hydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.0(3,11).0(4,7).0(9,11)]octadec-14-en-2-yl benzoate | C51H67NO14Si | 详情 | 详情 |