benzyl (3S,5S,6S)-2-<<2-<<(benzyloxy)carbonyl>amino>ethyl>thio>-6-<(R)-1-hydroxyethyl>carbapen-1-em-3-carboxylate | 70382-78-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl (3S,5S,6S)-2-<<2-<<(benzyloxy)carbonyl>amino>ethyl>thio>-6-<(R)-1-hydroxyethyl>carbapen-1-em-3-carboxylate
• CAS: 70382-78-4
• 化学式: C₂₆H₂₈N₂O₆S
• 分子量: 496.584
• InChiKey: HTCUSNGFAWRBMA-VZGVRVRRSA-N

反应信息

• 作为产物：
  描述：

  N-<(benzyloxy)carbonyl>thienamycin benzyl ester 在 1,5-Diazabicyclo[5.4.0]undec-5-ene 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 以29%的产率得到benzyl (3S,5S,6S)-2-<<2-<<(benzyloxy)carbonyl>amino>ethyl>thio>-6-<(R)-1-hydroxyethyl>carbapen-1-em-3-carboxylate
  参考文献：
  名称：

  Preparation and antibacterial activity of .DELTA.1-thienamycin

  摘要：

  delta 1-Thienamycin (2), a double-bond isomer of thienamycin, was prepared by isomerizing N-[[(p-nitrobenzyl)oxy]-carbonyl]thienamycin p-nitrobenzyl ester (5b) with DBU in Me2SO followed by hydrogenolysis of the protecting groups. When evaluated in a disc-diffusion antibacterial assay, delta 1-thienamycin was found to be essentially devoid of activity. The lack of antibacterial activity was ascribed to a chemically less reactive beta-lactam amide bond than that found in thienamycin.

  DOI：

  10.1021/jm00137a032