(2R,4S,5R)-2-(tert-butyl)-3-((S)-3-ethoxy-2-phenyl-3-oxopropanoyl)-4-methoxycarbonyl-5-methyloxazolidine | 1246373-60-3

• 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: (2R,4S,5R)-2-(tert-butyl)-3-((S)-3-ethoxy-2-phenyl-3-oxopropanoyl)-4-methoxycarbonyl-5-methyloxazolidine
• 英文别名: methyl (2R,4S,5R)-2-tert-butyl-3-[(2S)-3-ethoxy-3-oxo-2-phenylpropanoyl]-5-methyl-1,3-oxazolidine-4-carboxylate
• CAS: 1246373-60-3
• 化学式: C₂₁H₂₉NO₆
• 分子量: 391.464
• InChiKey: XOGLNCBVJVKOLV-WJCADGGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R)-2-(tert-butyl)-3-((S)-3-ethoxy-2-phenyl-3-oxopropanoyl)-4-methoxycarbonyl-5-methyloxazolidine 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 3.0h， 以67%的产率得到(2R,4R,5R)-1-aza-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-4-methyl-8-oxo-7-phenyl-3-oxabicyclo[3.3.0]oct-6-ene
  参考文献：
  名称：

  Novel chiral pyrrolidinone scaffolds derived from threonine with antibacterial activity

  摘要：

  The synthesis of chiral pyrrolidinones derived from threonine, making use of a Dieckmann or aldol ring closure, is described. Compounds were found to exhibit antibacterial activity, for which the correlation with various physiochemical parameters was examined. This chiral tetramate scaffold may provide a useful template for fragment-based drug design providing rapid access to novel antibacterial compound libraries. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.064
• 作为产物：
  描述：

  (2RS,4R,5S)-2-(tert-butyl)-5-methoxycarbonyl-4-methyl-1,3-oxazolidine 、 2-苯基-缩苹果酸单乙基酯 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以49%的产率得到(2R,4S,5R)-2-(tert-butyl)-3-((S)-3-ethoxy-2-phenyl-3-oxopropanoyl)-4-methoxycarbonyl-5-methyloxazolidine
  参考文献：
  名称：

  Novel chiral pyrrolidinone scaffolds derived from threonine with antibacterial activity

  摘要：

  The synthesis of chiral pyrrolidinones derived from threonine, making use of a Dieckmann or aldol ring closure, is described. Compounds were found to exhibit antibacterial activity, for which the correlation with various physiochemical parameters was examined. This chiral tetramate scaffold may provide a useful template for fragment-based drug design providing rapid access to novel antibacterial compound libraries. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.064

文献信息

• Novel chiral pyrrolidinone scaffolds derived from threonine with antibacterial activity
  作者：Muhammad Anwar、Andrew R. Cowley、Mark G. Moloney

  DOI：10.1016/j.tetasy.2010.04.064

  日期：2010.7

  The synthesis of chiral pyrrolidinones derived from threonine, making use of a Dieckmann or aldol ring closure, is described. Compounds were found to exhibit antibacterial activity, for which the correlation with various physiochemical parameters was examined. This chiral tetramate scaffold may provide a useful template for fragment-based drug design providing rapid access to novel antibacterial compound libraries. (C) 2010 Elsevier Ltd. All rights reserved.