(2R,3R,4S)-3,4-dimethyl-3-hydroxy-2-((R)-1-hydroxyethyl)-2-methoxycarbonyl-5-pyrrolidinone | 956227-02-4

• 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: (2R,3R,4S)-3,4-dimethyl-3-hydroxy-2-((R)-1-hydroxyethyl)-2-methoxycarbonyl-5-pyrrolidinone
• 英文别名: methyl (2R,3R,4S)-3-hydroxy-2-[(1R)-1-hydroxyethyl]-3,4-dimethyl-5-oxopyrrolidine-2-carboxylate
• CAS: 956227-02-4
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: ZHIYNCHCASJVBF-QLSQZMLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2R,4R,5R,6R,7S)-1-aza-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-4,6,7-trimethyl-8-oxo-3-oxabicyclo[3.3.0]octane 在 1,3-丙二硫醇 、 盐酸 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 7.0h， 以89%的产率得到(2R,3R,4S)-3,4-dimethyl-3-hydroxy-2-((R)-1-hydroxyethyl)-2-methoxycarbonyl-5-pyrrolidinone
  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