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【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