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【结 构 式】

【分子编号】10553

【品名】5-((1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-2-(benzoyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl) 3-(tert-butyl) (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate

【CA登记号】

【 分 子 式 】C51H60Cl3NO17

【 分 子 量 】1065.39204

【元素组成】C 57.5% H 5.68% Cl 9.98% N 1.31% O 25.53%

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:(XI)

3) The condensation of (4S,5R)-3-(bromoacetyl)-4-methyl-5-phenyloxazolidin-2-one (I) with benzaldehyde (II) by means of dibutylboron triflate gives intermediate (III), which by treatment with lithium ethoxide yields (R,R)-3-phenyloxirane-2-carboxylic acid ethyl ester (IV). The reaction of (IV) with sodium azide in ethanol affords the hydroxy ester (V), which is hydrogenated with H2 over Pd/C in ethyl acetate, giving the amino ester (VI). The protection of (VI) with tert-butoxycarbonyl anhydride affords the protected amino ester (VII), which is treated with 2-methoxypropene and pyridinium p-toluenesulfonate to give the oxazolidine (VIII). The hydrolysis of (VIII) with LiOH in ethanol/water yields (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid (IX), which is condensed with the protected baccatin III (X) by means of dicyclohexylcarbodiimide (DCC) and DMAP to afford the oxazolidine ester (XI). The treatment of (XI) with formic acid gives the amino ester (XII), which is benzoylated with benzoyl chloride and NaHCO3 to the protected paclitaxel (XIII). Finally, this compound is deprotected by treatment with Zn/acetic acid. (Commercon, A. et al. Tetrahedron Lett 1992, 33(36): 5185).

1 Guy, R.K.; Nicolaou, K.C.; Dai, W.M.; Chemistry and biology of taxol. Angew Chem. Int Ed Engl 1994, 33, 1, 15.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
63033 2-(ethyloxy)-1-propene; ethyl 1-methylethenyl ether C5H10O 详情 详情
(I) 10544 (4S,5R)-3-(2-Bromoacetyl)-4-methyl-5-phenyl-1,3-oxazolan-2-one C12H12BrNO3 详情 详情
(II) 10498 Benzaldehyde;Benzoic aldehyde;Phenylmethanal 100-52-7 C7H6O 详情 详情
(III) 10545 (4S,5R)-3-[(2S,3R)-2-Bromo-3-hydroxy-3-phenylpropanoyl]-4-methyl-5-phenyl-1,3-oxazolan-2-one C19H18BrNO4 详情 详情
(IV) 10546 ethyl (2R,3R)-3-phenyl-2-oxiranecarboxylate 121-39-1 C11H12O3 详情 详情
(V) 10547 ethyl (2R,3S)-3-azido-2-hydroxy-3-phenylpropanoate C11H13N3O3 详情 详情
(VI) 10548 ethyl (2R,3S)-3-amino-2-hydroxy-3-phenylpropanoate C11H15NO3 详情 详情
(VII) 10549 ethyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoate C16H23NO5 详情 详情
(VIII) 10550 3-(tert-butyl) 5-ethyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate C19H27NO5 详情 详情
(IX) 10551 (4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolane-5-carboxylic acid C17H23NO5 详情 详情
(X) 10448 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C34H39Cl3O13 详情 详情
(XI) 10553 5-((1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-2-(benzoyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl) 3-(tert-butyl) (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate C51H60Cl3NO17 详情 详情
(XII) 10554 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C43H48Cl3NO15 详情 详情
(XIII) 10555 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C43H48Cl3NO15 详情 详情
Extended Information