Author/Authors :
Xiong, Fei Hubei Key Laboratory of Drug Synthesis and Optimization - JingChu University of Technology, Jingmen, China , Li, Gen Department of Chemistry - University of Shanghai for Science and Technology, Shanghai, China , Song, Bo Hubei Key Laboratory of Drug Synthesis and Optimization - JingChu University of Technology, Jingmen, China , Chen, Fen-Er Department of Chemistry - Fudan University, Shanghai, China , Zeng, Zhao-Sen Department of Chemistry - Fudan University, Shanghai, China
Abstract :
An efficient and practical seven-step procedure is described for the synthesis of (6R,7S)-benzhydryl-7-amino-7-methoxy-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-aza-bicyclo [4.2.0]oct-2-ene-2-carboxylate (7-MAC, 3) with overall yield of 49 %. This synthesis features a convenient and highly selective method for the introduction of 7α-methoxy group to cephalosporin nucleus in 10 using MeOLi/t-BuOCl in THF.
Keywords :
Antibiotics , Esterification , Isomerization , 7α-Methoxycephalosporins , Stereoselectivity synthesis
