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新产品编号:1902073

Chemical Name: 3-[3-Amino-3-oxo-1(E)-propenyl]-1,1-dioxo-7-[(Z)-2-pyridylmethylene]-3-cephem-4-carboxylic acid sodium salt
项目整合开发状态: Biological Testing
项目研究机构: Southern Methodist University (Originator)
合成路线:Cephalosporanate (I) was equilibrated with its delta-2,3 isomer (II) by treatment with Et3N.Isomer (II) was then carefully hydrolyzed to alcohol (III) without formation of the corresponding lactone by-product.The oxidation of alcohol (III) with pyridinium dichromate gave aldehyde (IV),which was subjected to a Wittig condensation with phosphorane (V) to produce the unsaturated E-amide (VI) as the major isomer.Sulfur oxidation with MCPBA,with concomitant double bond isomerization,furnished sulfone (VII).Finally,removal of the benzhydryl protecting group with trifluoroacetic acid,followed by treatment with sodium bicarbonate yielded the title sodium carboxylate salt.
📌 参考资料/链接:
参考文献标题:The synthesis and evaluation of 3-substituted-7-(alkylidene)cephalosporin sulfones as beta-lactamase inhibitors
文献作者:Buynak,J.D.; Doppalapudi,R.; Adam,G.
参考来源:Bioorg Med Chem Lett 2000,10(9),853