(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 | 956226-96-3

• 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,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
• 英文别名: methyl (1R,3R,6S,7R,7aR)-3-tert-butyl-7-hydroxy-1,6,7-trimethyl-5-oxo-3,6-dihydro-1H-pyrrolo[1,2-c][1,3]oxazole-7a-carboxylate
• CAS: 956226-96-3
• 化学式: C₁₅H₂₅NO₅
• 分子量: 299.367
• InChiKey: RLZDGPMAXFKROA-WMPUKIQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  methyl (2R,4S,5R)-2-tert-butyl-5-methyl-3-(2-methyl-3-oxobutanoyl)-1,3-oxazolidine-4-carboxylate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以12%的产率得到(2R,4R,5R,6S,7S)-1-aza-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-4,6,7-trimethyl-8-oxo-3-oxabicyclo[3.3.0]octane
  参考文献：
  名称：

  从苏氨酸高效合成对苯二甲酸和内酰胺

  摘要：

  使用衍生自苏氨酸的N-酰基氧唑烷进行的区域选择性Dieckmann和aldol环化反应可高产率和对映选择性地获得取代的四酸和焦谷氨酸。这些在温和的条件下很容易脱保护，得到一些具有抗菌活性的产品。

  DOI：

  10.1016/j.tetlet.2007.08.052

文献信息

• Efficient enantioselective synthesis of tetramic acids and lactams from threonine
  作者：Muhammad Anwar、Mark G. Moloney

  DOI：10.1016/j.tetlet.2007.08.052

  日期：2007.10

  Regioselective Dieckmann and aldol cyclisations using an N-acyloxazolidine derived from threonine give substituted tetramic acids and pyroglutamates in high yield and enantioselectivity. These are easily deprotected under mild conditions to give products, some of which exhibit antibacterial activity.

  使用衍生自苏氨酸的N-酰基氧唑烷进行的区域选择性Dieckmann和aldol环化反应可高产率和对映选择性地获得取代的四酸和焦谷氨酸。这些在温和的条件下很容易脱保护，得到一些具有抗菌活性的产品。
• 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.