【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% |
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 |