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

作者：Xiong, Fei^*; Li, Gen; Song, Bo; Chen, Fen-Er; Zeng, Zhao-Sen

来源：Journal of the Iranian Chemical Society, 2016, 13(6): 1019-1025.

DOI：10.1007/s13738-016-0815-0

• Antibiotics
• Esterification
• Isomerization
• 7 alpha-Methoxycephalosporins
• Stereoselectivity synthesis

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 7 alpha-methoxy group to cephalosporin nucleus in 10 using MeOLi/t-BuOCl in THF.

• 出版日期2016-6
• 单位荆楚理工学院; 上海理工大学; 复旦大学