【结 构 式】 |
【分子编号】46695 【品名】4-nitrobenzyl (4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate 【CA登记号】 |
【 分 子 式 】C17H18N2O7 【 分 子 量 】362.3392 【元素组成】C 56.35% H 5.01% N 7.73% O 30.91% |
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:(III)Cyclization of azetidinone (I) by means of catalyst Rh2(OAc)4 in toluol provides carbapenam (II), which is treated with SiO2 in EtOAc to produce epimerization to the alpha-methyl compound (III). Methylation of (III) with diazomethane in dioxane affords carbapenem (IV), which is hydrogenolyzed over Pd/C in EtOAc and finally saponified with KHCO3 in H2O to furnish the desired compound.
【1】 Weishaupt, R.; Pfaendler, H.R.; Meffert, H.; Synthesis and biological activities of an alpha-methyl and a beta-methyl carbapenem and the corresponding unsubstituted compound. Bioorg Med Chem Lett 2000, 10, 12, 1389. |
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) | 38749 | 4-nitrobenzyl (4R)-2-diazo-4-[(2R,3S)-3-[(1R)-1-hydroxyethyl]-4-oxoazetidinyl]-3-oxopentanoate | C17H18N4O7 | 详情 | 详情 | |
(II) | 37720 | 4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate | C17H18N2O7 | 详情 | 详情 | |
(III) | 46695 | 4-nitrobenzyl (4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate | C17H18N2O7 | 详情 | 详情 | |
(IV) | 46696 | 4-nitrobenzyl (4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-3-methoxy-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C18H20N2O7 | 详情 | 详情 |
Extended Information