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【结 构 式】 
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【分子编号】30869 【品名】tert-butyl (2R,4R)-4-[[tert-butyl(dimethyl)silyl]oxy]-2-(4-[(1R)-3-ethoxy-1-[(methylsulfonyl)oxy]-3-oxopropyl]phenyl)-1-pyrrolidinecarboxylate 【CA登记号】 |
【 分 子 式 】C27H45NO8SSi 【 分 子 量 】571.80774 【元素组成】C 56.71% H 7.93% N 2.45% O 22.38% S 5.61% Si 4.91% |
合成路线1
该中间体在本合成路线中的序号：(XVII)In an alternative procedure, aldehyde (IV) was condensed with ethyl acetate in the presence of lithium hexamethyldisilazide to give hydroxyester (XIII). This was esterified with chloroacetyl chloride to provide (XIV) as a diastereomeric mixture. Kinetic resolution of (XIV) employing lipase selectively hydrolyzed the required isomer to furnish hydroxyester (XVI), which was separated from the undesired chloroacetate (XV). Alcohol (XVI) was converted to mesylate (XVII). Subsequent displacement in (XVII) by NaN3 afforded the corresponding azide, which was reduced to amine (IX) by hydrogenation over Pd/C. This was finallyconverted to the title compound by the same sequence as above.
| 【1】 Imamura, H.; Sato, H.; Shimizu, A.; et al.; J-114,870 and J-114,871, novel trans-3,5-disubstituted pyrrolidinylthio 1beta-methylcarbapenems: Synthesis and physicochemical properties. 38th Intersci Conf Antimicrob Agents Chemother (Sept 24 1998, San Diego) 1998, Abst F-56. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 30852 | tert-butyl (2R,4R)-4-[[tert-butyl(dimethyl)silyl]oxy]-2-(4-formylphenyl)-1-pyrrolidinecarboxylate | C22H35NO4Si | 详情 | 详情 | |
| (IX) | 30856 | tert-butyl (2R,4R)-2-[4-[(1R)-1-amino-3-ethoxy-3-oxopropyl]phenyl]-4-[[tert-butyl(dimethyl)silyl]oxy]-1-pyrrolidinecarboxylate | C26H44N2O5Si | 详情 | 详情 | |
| (XIII) | 30859 | tert-butyl (2R,4R)-4-[[tert-butyl(dimethyl)silyl]oxy]-2-[4-(3-ethoxy-1-hydroxy-3-oxopropyl)phenyl]-1-pyrrolidinecarboxylate | C26H43NO6Si | 详情 | 详情 | |
| (XIV) | 30860 | tert-butyl (2R,4R)-4-[[tert-butyl(dimethyl)silyl]oxy]-2-(4-[1-[(2-chloroacetyl)oxy]-3-ethoxy-3-oxopropyl]phenyl)-1-pyrrolidinecarboxylate | C28H44ClNO7Si | 详情 | 详情 | |
| (XV) | 30862 | tert-butyl (2R,4R)-4-[[tert-butyl(dimethyl)silyl]oxy]-2-(4-[(1S)-1-[(2-chloroacetyl)oxy]-3-ethoxy-3-oxopropyl]phenyl)-1-pyrrolidinecarboxylate | C28H44ClNO7Si | 详情 | 详情 | |
| (XVI) | 30861 | tert-butyl (2R,4R)-4-[[tert-butyl(dimethyl)silyl]oxy]-2-[4-[(1R)-3-ethoxy-1-hydroxy-3-oxopropyl]phenyl]-1-pyrrolidinecarboxylate | C26H43NO6Si | 详情 | 详情 | |
| (XVII) | 30869 | tert-butyl (2R,4R)-4-[[tert-butyl(dimethyl)silyl]oxy]-2-(4-[(1R)-3-ethoxy-1-[(methylsulfonyl)oxy]-3-oxopropyl]phenyl)-1-pyrrolidinecarboxylate | C27H45NO8SSi | 详情 | 详情 |