4-nitrobenzyl 2-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2-(formylthio)-4-oxoazetidin-1-yl)-3-methylbut-2-enoate | 1186219-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 4-nitrobenzyl 2-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2-(formylthio)-4-oxoazetidin-1-yl)-3-methylbut-2-enoate
• CAS: 1186219-02-2
• 化学式: C₂₄H₃₄N₂O₇SSi
• 分子量: 522.695
• InChiKey: SGXDZKGYGAYKFL-GTCCEBARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  116.05
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-nitrobenzyl 2-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2-(formylthio)-4-oxoazetidin-1-yl)-3-methylbut-2-enoate 在 臭氧 作用下， 以 乙酸乙酯 为溶剂， 以98%的产率得到4-nitrobenzyl 2-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2-(formylthio)-4-oxoazetidin-1-yl)-2-oxoacetate
  参考文献：
  名称：

  Synthesis and biological evaluation of penem inhibitors of bacterial signal peptidase

  摘要：

  We report the first synthesis of a 5S penem, known to bind bacterial type I signal peptidase, from the commercially available and inexpensive 6-aminopenicillanic acid. We report the first in vivo activity of the compound and use structure-activity relationship studies to begin to define the determinants of signal peptidase binding and also to begin to optimize the penem as an antibiotic. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.034
• 作为产物：
  描述：

  甲酸 、 (4-nitrophenyl)methyl 2-[(2R,3S)-2-(1,3-benzothiazol-2-yldisulfanyl)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-1-yl]-3-methylbut-2-enoate 在 吡啶 、 乙酸酐 、 三苯基膦 作用下， 以 甲苯 为溶剂， 生成 4-nitrobenzyl 2-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2-(formylthio)-4-oxoazetidin-1-yl)-3-methylbut-2-enoate
  参考文献：
  名称：

  Synthesis and biological evaluation of penem inhibitors of bacterial signal peptidase

  摘要：

  We report the first synthesis of a 5S penem, known to bind bacterial type I signal peptidase, from the commercially available and inexpensive 6-aminopenicillanic acid. We report the first in vivo activity of the compound and use structure-activity relationship studies to begin to define the determinants of signal peptidase binding and also to begin to optimize the penem as an antibiotic. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.034