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【结 构 式】

【药物名称】

【化学名称】(1S,5R,6S)-6-[1(R)-Hydroxyethyl]-2-methoxy-1-methyl-1-carba-2-penem-3-carboxylic acid potassium salt

【CA登记号】

【 分 子 式 】C11H14KNO5

【 分 子 量 】279.33993

【开发单位】Ludwig-Maximilians-Univ. München (Originator)

【药理作用】Antibiotics, ANTIINFECTIVE THERAPY, beta-Lactamase Inhibitors, Carbapenems

合成路线1

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