首页> 外文期刊>The Journal of Antibiotics: An International Journal >Isolation and characterization of side-products formed through Delta 2-isomerization in the synthesis of cefpodoxime proxetil
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Isolation and characterization of side-products formed through Delta 2-isomerization in the synthesis of cefpodoxime proxetil

机译:Cefpodoxime Proxetil合成中δ2-异构化形成的侧产物的分离与表征

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摘要

In the synthesis of cephalosporin antibiotics, esterified in 4-position, the Delta 2-isomerization is a well-known side reaction proceeding under basic conditions. In this work, we investigated the Delta 2-isomerization of the esterified cefpodoxime proxetil. Due to the R-configuration and S-configuration of the stereogenic center in the side chain in 4-position, there are two starting materials being diastereomeric to each other. Furthermore, an additional stereogenic center is formed in the isomerization step, thus leading to four possible products. To the best of our knowledge, in this work for the first time the Delta 2-isomerization of the two isolated diastereomers of AMCA proxetil, a precursor of cefpodoxime proxetil, as a starting material is reported. It has been shown, that each diastereomer only reacts to one of the two possible Delta 2-diastereomers. The synthesis, isolation and characterization of (R)-diastereomers as well as (S)-diastereomers of Delta 2-AMCA proxetil and cefpodoxime proxetil, respectively, are presented.
机译:在1-位酯化的Cephalosporin抗生素的合成中,Delta 2-异构化是在碱性条件下进行众所周知的副反应。在这项工作中,我们研究了酯化的头孢会课程的Delta 2异构化。由于4位的侧链的立体中心的r-配置和s-配置,有两个起始材料彼此不熟化。此外,在异构化步骤中形成另外的立体化中心,从而导致四种可能的产品。据报道,据我们所知,在这项工作中,首次首次达到AMCA Proxetil的两个分离的非对映异构体的Δ2-异构化,作为起始材料,是头孢哌甲段的前体。已经表明,每个非对映异构体仅对两种可能的Delta 2-非对映异构体之一反应。提出了(R)-DiaSteRemers的合成,分离和表征,以及分别的Delta 2-AMCA proxetil和Cefpodoxime Proxetil的 - DiaSteRemers。

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