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【结 构 式】 
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【分子编号】37808 【品名】(2R,3S,4R)-3-hydroxy-2-[(1R)-1-hydroxy-2-methylpropyl]-5-oxo-4-propyl-2-pyrrolidinecarboxylic acid 【CA登记号】 |
【 分 子 式 】C12H21NO5 【 分 子 量 】259.30248 【元素组成】C 55.58% H 8.16% N 5.4% O 30.85% |
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：(XXI)Treatment of the lithium enolate of oxazoline ester (XVIII) with dimethylaluminum chloride, followed by aldol condensation with aldehyde (IX) at -80 C diastereoselectively led to adduct (XIX). Hydrogenolysis of the oxazoline (XIX) with concomitant cyclization of the intermediate aminodiol produced lactam (XX). The methyl ester group of (XX) was then hydrolyzed with NaOH to give hydroxyacid (XXI). This was finally cyclized to the title lactone employing either TBTU or isopropenyl chloroformate in the presence of Et3N.
| 【1】 Soucy, F.; et al.; A novel and efficient synthesis of a highly active analogue clasto-lactacystin beta-lactone. J Am Chem Soc 1999, 121, 43, 9967. |
| 【2】 Plamondon, L.; Adams, J.; Elliot, P. (ProScript, Inc.); Proteasome inhibitors, ubiquitin pathway inhibitors or agents that interfere with the activation of NF-kappaB via the ubiquitin proteasome pathway to treat inflammatory and autoimmune diseases. WO 9915183 . |
| 【3】 Plamondon, L.; Soucy, F.; Behnke, M.; Roush, W.; Synthesis of clasto-lactacystin beta-lactone and analogs thereof. WO 9909006 . |
| 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) | 37798 | (2R)-N,N-diethyl-2-formylpentanamide | C10H19NO2 | 详情 | 详情 | |
| (XVIII) | 37805 | methyl (4R,5S)-5-isopropyl-2-phenyl-4,5-dihydro-1,3-oxazole-4-carboxylate | C14H17NO3 | 详情 | 详情 | |
| (XIX) | 37806 | methyl (4S,5S)-4-[(1S,2R)-2-[(diethylamino)carbonyl]-1-hydroxypentyl]-5-isopropyl-2-phenyl-4,5-dihydro-1,3-oxazole-4-carboxylate | C24H36N2O5 | 详情 | 详情 | |
| (XX) | 37807 | methyl (2R,3S,4R)-3-hydroxy-2-[(1R)-1-hydroxy-2-methylpropyl]-5-oxo-4-propyl-2-pyrrolidinecarboxylate | C13H23NO5 | 详情 | 详情 | |
| (XXI) | 37808 | (2R,3S,4R)-3-hydroxy-2-[(1R)-1-hydroxy-2-methylpropyl]-5-oxo-4-propyl-2-pyrrolidinecarboxylic acid | C12H21NO5 | 详情 | 详情 |
Extended Information