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A novel synthetic route to 7-MAC from 7-ACA

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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.

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Acknowledgments

The authors gratefully acknowledge the financial support from Shanghai Municipal Education Commission (No. SLG14033) and the open project program of Hubei Key Laboratory of Drug Synthesis and Optimization, JingChu University of Technology (No. OPP2014ZD01).

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Authors and Affiliations

  1. Department of Chemistry, University of Shanghai for Science and Technology, Shanghai, 200093, China

    Fei Xiong, Gen Li & Bo Song

  2. Department of Chemistry, Fudan University, Shanghai, 200433, China

    Fei Xiong, Fen-Er Chen & Zhao-Sen Zeng

  3. Hubei Key Laboratory of Drug Synthesis and Optimization, JingChu University of Technology, Jingmen, 448000, China

    Fei Xiong

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  1. Fei Xiong
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  2. Gen Li
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Correspondence to Fei Xiong.

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Xiong, F., Li, G., Song, B. et al. A novel synthetic route to 7-MAC from 7-ACA. J IRAN CHEM SOC 13, 1019–1025 (2016). https://doi.org/10.1007/s13738-016-0815-0

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  • DOI: https://doi.org/10.1007/s13738-016-0815-0

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