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【结 构 式】 
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【分子编号】43284 【品名】(9S)-9-[(tert-butoxycarbonyl)amino]-3-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene-2-carboxylic acid 【CA登记号】 |
【 分 子 式 】C24H35NO5 【 分 子 量 】417.54564 【元素组成】C 69.04% H 8.45% N 3.35% O 19.16% |
合成路线1
该中间体在本合成路线中的序号：(XXII)An alternative procedure has been reported for the synthesis of the chiral (S)-amine (XXIV). Ketone (IX) was treated with O-methyl hydroxylamine to afford a geometric mixture of O-methyl oximes, from which isomer (XVII) was isolated by silica gel chromatography. Asymmetric reduction of the O-methyl oxime (XVII) with borane in the presence of the chiral auxiliary (XVIII) furnished the desired (S)-amine (XIX), which was further protected as the tert-butyl carbamate (XX) by treatment with Boc2O. Bromide (XXI), carboxylic acid (XXII) and amide (XXIII) were obtained following the same procedures as above. Then, acid cleavage of the Boc group of (XXIII) yielded the chiral amine (XXIV).
| 【1】 Bohacek, R.; Yang, M.; Shakespeare, W.; et al.; Structure-based design of an osteoclast-selective, nonpeptide Src homology 2 inhibitor with in vivo antiresorptive activity. Proceedings of the National Academy of Sciences of the United States of America 2000, 97, 17, 9373. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX) | 43271 | 2-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one | C18H24O2 | 详情 | 详情 | |
| (XVII) | 43279 | 2-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one O-methyloxime | C19H27NO2 | 详情 | 详情 | |
| (XVIII) | 10103 | (2R)-2-Amino-3-methyl-1,1-diphenyl-1-butanol | 56755-20-5 (hydrochloride) | C17H21NO | 详情 | 详情 |
| (XIX) | 43281 | (5S)-2-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ylamine; (5S)-2-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-amine | C18H27NO | 详情 | 详情 | |
| (XX) | 43282 | tert-butyl (5S)-2-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ylcarbamate | C23H35NO3 | 详情 | 详情 | |
| (XXI) | 43283 | tert-butyl (5S)-3-bromo-2-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ylcarbamate | C23H34BrNO3 | 详情 | 详情 | |
| (XXII) | 43284 | (9S)-9-[(tert-butoxycarbonyl)amino]-3-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene-2-carboxylic acid | C24H35NO5 | 详情 | 详情 | |
| (XXIII) | 43285 | tert-butyl (5S)-3-(aminocarbonyl)-2-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ylcarbamate | C24H36N2O4 | 详情 | 详情 | |
| (XXIV) | 43286 | (9S)-9-amino-3-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene-2-carboxamide | C19H28N2O2 | 详情 | 详情 |