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【结 构 式】

【分子编号】67593

【品名】(2R,4aS,4bR,6aR,9aR,9bS,9cS,12aS)-4a,6a,11,11-tetramethyl-7-methylenehexadecahydro-1H-cyclopenta[1,2]phenanthro[9,10-d][1,3]dioxol-2-yl acetate

【CA登记号】 

【 分 子 式 】C25H38O4

【 分 子 量 】402.57432

【元素组成】C 74.59% H 9.51% O 15.9%

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: (XVI)

Treatment of compound (XV) with Ac2O and DMAP in pyridine yields acetate (XVI), which by hydrolysis with AcOH produces diol (XVII). Oxidative cleavage of diol (XVII) by means of NaIO4 in H2O/THF provides dialdehyde (XVIII), which is reduced with NaBH4 in MeOH/THF to afford the corresponding diol (XIX). Selectively monoesterification of diol (XIX) with Ac2O in the presence of DMAP in pyridine produces acetate (XX), which is treated with MsCl in pyridine to obtain mesylate (XXI). Treatment of compound (XXI) with NaN3 in DMF at 60 °C results in azide (XXII), which is finally reduced with LiAlH4 in THF and treated with AcOH .

1 Yee, J.G.K., Raymond, J.R., He, Y., Noren, B., Han, K., Zhou, Y. (Aquinox Pharmaceuticals). Indene derivatives as pharmaceutical agents. CN 102010298; CN 102001916; JP 2011068677; US 7999010; US 2014371252; US 8084503; EP 1615866; EP 2277848; US 2005004086; US 2011172258; US 8673975; US 7601874; JP 2006523624; US 2012270901; WO 2004092100; CA 2521883.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XVI) 67593 (2R,4aS,4bR,6aR,9aR,9bS,9cS,12aS)-4a,6a,11,11-tetramethyl-7-methylenehexadecahydro-1H-cyclopenta[1,2]phenanthro[9,10-d][1,3]dioxol-2-yl acetate   C25H38O4 详情 详情
(XIV) 67591 (2R,4aS,4bR,6aR,9aR,9bS,9cS,12aS)-2-hydroxy-4a,6a,11,11-tetramethyltetradecahydro-1H-cyclopenta[1,2]phenanthro[9,10-d][1,3]dioxol-7(8H)-one   C22H34O4 详情 详情
(XV) 67592 (2R,4aS,4bR,6aR,9aR,9bS,9cS,12aS)-4a,6a,11,11-tetramethyl-7-methylenehexadecahydro-1H-cyclopenta[1,2]phenanthro[9,10-d][1,3]dioxol-2-ol   C23H36O3 详情 详情
(XVII) 67594 (2R,4aS,4bR,6aR,9aR,9bS,9cS,12aS)-4a,6a,11,11-tetramethyl-7-methylenehexadecahydro-1H-cyclopenta[1,2]phenanthro[9,10-d][1,3]dioxol-2-yl acetate   C22H34O4 详情 详情
(XVIII) 67595 (1R,3R,4S)-3-formyl-4-((3aR,4R,5R,7aR)-4-formyl-7a-methyl-1-methyleneoctahydro-1H-inden-5-yl)-4-methylcyclohexyl acetate   C22H32O4 详情 详情
(XIX) 67596 (1R,3R,4S)-3-(hydroxymethyl)-4-((3aR,4R,5R,7aR)-4-(hydroxymethyl)-7a-methyl-1-methyleneoctahydro-1H-inden-5-yl)-4-methylcyclohexyl acetate   C22H36O4 详情 详情
(XX) 67597 ((1R,2S,5R)-5-acetoxy-2-((3aR,4R,5R,7aR)-4-(hydroxymethyl)-7a-methyl-1-methyleneoctahydro-1H-inden-5-yl)-2-methylcyclohexyl)methyl acetate   C24H38O5 详情 详情
(XXI) 67598 ((1R,2S,5R)-5-acetoxy-2-methyl-2-((3aR,4R,5R,7aR)-7a-methyl-1-methylene-4-(((methylsulfonyl)oxy)methyl)octahydro-1H-inden-5-yl)cyclohexyl)methyl acetate   C25H40O7S 详情 详情
(XXII) 67599 ((1R,2S,5R)-5-acetoxy-2-((3aR,4R,5R,7aR)-4-(azidomethyl)-7a-methyl-1-methyleneoctahydro-1H-inden-5-yl)-2-methylcyclohexyl)methyl acetate   C24H37N3O4 详情 详情
(XXIII) 67600 (1R,3R,4S)-4-((3aR,4R,5R,7aR)-4-(aminomethyl)-7a-methyl-1-methyleneoctahydro-1H-inden-5-yl)-3-(hydroxymethyl)-4-methylcyclohexanol   C20H35NO2 详情 详情
Extended Information