(3R,5S)-5-((S)-1-azido-3-methylbutyl)-3-methyldihydrofuran-2(3H)-one | 1292778-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,5S)-5-((S)-1-azido-3-methylbutyl)-3-methyldihydrofuran-2(3H)-one
• 英文别名: (3R,5S)-5-[(1S)-1-azido-3-methylbutyl]-3-methyloxolan-2-one
• CAS: 1292778-98-3
• 化学式: C₁₀H₁₇N₃O₂
• 分子量: 211.264
• InChiKey: XFLPVIMKWRQTCQ-VGMNWLOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,5S)-5-((S)-1-azido-3-methylbutyl)-3-methyldihydrofuran-2(3H)-one 在 palladium 10% on activated carbon 、 水 、 氢气 、 lithium hydroxide 作用下， 以 乙二醇二甲醚 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 (2R,4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-2,7-dimethyl-octanoic acid
  参考文献：
  名称：

  On a Possible Neutral Charge State for the Catalytic Dyad in β-Secretase When Bound to Hydroxyethylene Transition State Analogue Inhibitors

  摘要：

  beta-Secretase is one of the aspartic proteases involved in the formation of amyloid plaques in Alzheimer's disease patients Our previous results using a combination of surface plasmon resonance experiments with molecular Modeling calculations: suggested that the Asp dyad in beta-secretase bound to hydroxylethylene containing inhibitors adopts a neutral charged state. In this work, we show that the Asp dyad diprotonated state reproduced the binding ranking of a set of these inhibitors better than alternative protonation states.

  DOI：

  10.1021/jm101568y
• 作为产物：
  描述：

  5,6-anhydro-2,3-dideoxy-D-erythro-hexono-1,4-lactone 在 吡啶 、 sodium azide 、 lithium chloride 、 copper dichloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 (3R,5S)-5-((S)-1-azido-3-methylbutyl)-3-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  On a Possible Neutral Charge State for the Catalytic Dyad in β-Secretase When Bound to Hydroxyethylene Transition State Analogue Inhibitors

  摘要：

  beta-Secretase is one of the aspartic proteases involved in the formation of amyloid plaques in Alzheimer's disease patients Our previous results using a combination of surface plasmon resonance experiments with molecular Modeling calculations: suggested that the Asp dyad in beta-secretase bound to hydroxylethylene containing inhibitors adopts a neutral charged state. In this work, we show that the Asp dyad diprotonated state reproduced the binding ranking of a set of these inhibitors better than alternative protonation states.

  DOI：

  10.1021/jm101568y