LB-11058
Chemical Name: (6R,7R)-7-[(Z)-2-(2-Amino-5-chlorothiazol-4-yl)-2-(hydroxyimino)acetamido]-3-[(E)-2-(2-amino-6-hydroxypyrimidin-4-ylsulfanyl)vinyl]-3-cephem-4-carboxylic acid
项目整合开发状态: Preclinical
项目研究机构: LG Chem (Originator)
合成路线:Coupling of the amino cephem derivative (I) with oximino acid (II) by means of POCl3/pyridine produces amide (III).Subsequent condensation of (III) with bis(dimethylamino)t-butoxymethane affords enamine (IV),which is further hydrolyzed to aldehyde (V) under acidic conditions.Treatment of aldehyde (V) with trifluoromethanesulfonic anhydride and pyridine produces the vinyl triflate (VI)
合成路线:Displacement of the triflate group of (VI) with the pyrimidinyl thiol (VII) yields the vinyl sulfide (VIII).Then,deprotection of (VIII) by means of trifluoroacetic acid and triethylsilane gives rise to the title compound
📌 参考资料/链接：
参考文献标题:Novel cephalosporin cpds.and process for preparing the same
文献作者:Lee,S.-H.; Lee,C.-S.; Ryu,E.-J.; Jang,Y.-J.; Kim,G.-T.; Cho,Y.-r.; Joo,H.-Y.; Shin,J.-E.; Koo,K.-D.(LG Chem Ltd.)
参考来源:WO 0372582
📄 详细内容
合成路线:Coupling of the amino cephem derivative (I) with oximino acid (II) by means of POCl3/pyridine produces amide (III).Subsequent condensation of (III) with bis(dimethylamino)t-butoxymethane affords enamine (IV),which is further hydrolyzed to aldehyde (V) under acidic conditions.Treatment of aldehyde (V) with trifluoromethanesulfonic anhydride and pyridine produces the vinyl triflate (VI)
合成路线:Displacement of the triflate group of (VI) with the pyrimidinyl thiol (VII) yields the vinyl sulfide (VIII).Then,deprotection of (VIII) by means of trifluoroacetic acid and triethylsilane gives rise to the title compound
参考文献标题:Synthesis and antibacterial activities of LB11058,a novel anti-MRSA cephalosporin antibiotic
文献作者:Lee,C.; Kim,G.; Jang,Y.; Koo,K.; Cho,Y.; Youn,H.
参考来源:42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002,San Diego) 2002,Abst F-329