【结 构 式】 |
【分子编号】59662 【品名】3-amino-4-{[tert-butyl(diphenyl)silyl]oxy}phenyl acetate 【CA登记号】 |
【 分 子 式 】C24H27NO3Si 【 分 子 量 】405.56882 【元素组成】C 71.08% H 6.71% N 3.45% O 11.83% Si 6.92% |
合成路线1
该中间体在本合成路线中的序号:(IV)The chiral epoxide (VIII) was prepared as follows. 4-Hydroxy-3-nitroacetophenone (I) was protected as the silyl derivative (II) and then subjected to a Baeyer-Villiger rearrangement to afford the phenol acetate ester (III). Hydrogenation of the nitro group of (III) over Raney nickel provided aniline (IV), which was acylated by methanesulfonyl chloride producing sulfonamide (V). After protection of the sulfonamide NH of (V) with Boc2O, basic hydrolysis of the acetate ester furnished phenol (VI). Mitsunobu coupling between phenol (VI) and (R)-glycidol (VII) led to the glycidyl ether (VIII).
【1】 Mulvey, R.; Ashwell, M.A.; Solvibile, W.R. Jr.; Han, S.; Tillet, J.; Largis, E.; 4-Aminopiperidine ureas as potent selective agonists of the human beta3-adrenergic receptor. Bioorg Med Chem Lett 2001, 11, 24, 3123. |
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) | 20626 | 1-(4-hydroxy-3-nitrophenyl)-1-ethanone | 6322-56-1 | C8H7NO4 | 详情 | 详情 |
(II) | 59660 | 1-(4-{[tert-butyl(diphenyl)silyl]oxy}-3-nitrophenyl)-1-ethanone | C24H25NO4Si | 详情 | 详情 | |
(III) | 59661 | 4-{[tert-butyl(diphenyl)silyl]oxy}-3-nitrophenyl acetate | C24H25NO5Si | 详情 | 详情 | |
(IV) | 59662 | 3-amino-4-{[tert-butyl(diphenyl)silyl]oxy}phenyl acetate | C24H27NO3Si | 详情 | 详情 | |
(V) | 59663 | 4-{[tert-butyl(diphenyl)silyl]oxy}-3-[(methylsulfonyl)amino]phenyl acetate | C25H29NO5SSi | 详情 | 详情 | |
(VI) | 59664 | tert-butyl 2-{[tert-butyl(diphenyl)silyl]oxy}-5-hydroxyphenyl(methylsulfonyl)carbamate | C28H35NO6SSi | 详情 | 详情 | |
(VII) | 16206 | (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-2-[2-(4-nitrobenzyloxy)acetyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl diphenylphosphinate | C29H27N2O8P | 详情 | 详情 | |
(VIII) | 59665 | tert-butyl 2-{[tert-butyl(diphenyl)silyl]oxy}-5-[(2S)oxiranylmethoxy]phenyl(methylsulfonyl)carbamate | C31H39NO7SSi | 详情 | 详情 |