(2R,3R,5R,6S)-2-(((R)-5-methoxy-5-oxopentan-2-yl)oxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate | 1172590-13-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,5R,6S)-2-(((R)-5-methoxy-5-oxopentan-2-yl)oxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate
• CAS: 1172590-13-4
• 化学式: C₂₆H₃₀O₈
• 分子量: 470.519
• InChiKey: SLEGSIZMFHQOCV-BXRCKUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,5R,6S)-2-(((R)-5-methoxy-5-oxopentan-2-yl)oxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate 在 甲醇 、 sodium 作用下， 反应 2.0h， 以91%的产率得到methyl (4R)-4-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxypentanoate
  参考文献：
  名称：

  An Indole-Containing Dauer Pheromone Component with Unusual Dauer Inhibitory Activity at Higher Concentrations

  摘要：

  In Caenorhabditis elegans, the dauer pheromone, which consists of a number of derivatives of the 3,6-dideoxysugar ascarylose, is the primary cue for entry into the stress-resistant, "nonaging" dauer larval stage. Here, using activity-guided fractionation and NMR-based structure elucidation, a structurally novel, indole-3-carboxyl-modified ascaroside is identified that promotes dauer formation at low nanomolar concentrations but inhibits dauer formation at higher concentrations.

  DOI：

  10.1021/ol901011c
• 作为产物：
  描述：

  甲醇 、 (R)-4-(((2R,3R,5R,6S)-3,5-bis(benzoyloxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)pentanoic acid 在 溶剂黄146 、 三甲基硅烷化重氮甲烷 作用下， 以 乙醚 为溶剂， 以135.2 mg的产率得到(2R,3R,5R,6S)-2-(((R)-5-methoxy-5-oxopentan-2-yl)oxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate
  参考文献：
  名称：

  An Indole-Containing Dauer Pheromone Component with Unusual Dauer Inhibitory Activity at Higher Concentrations

  摘要：

  In Caenorhabditis elegans, the dauer pheromone, which consists of a number of derivatives of the 3,6-dideoxysugar ascarylose, is the primary cue for entry into the stress-resistant, "nonaging" dauer larval stage. Here, using activity-guided fractionation and NMR-based structure elucidation, a structurally novel, indole-3-carboxyl-modified ascaroside is identified that promotes dauer formation at low nanomolar concentrations but inhibits dauer formation at higher concentrations.

  DOI：

  10.1021/ol901011c