(1R)-1-[(3S,5R)-3-allyl-2-benzyl-3-isobutylisoxazolidin-5-yl]-2-(tert-butyldimethylsilanyloxy)ethanol | 866483-36-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1R)-1-[(3S,5R)-3-allyl-2-benzyl-3-isobutylisoxazolidin-5-yl]-2-(tert-butyldimethylsilanyloxy)ethanol
• CAS: 866483-36-5
• 化学式: C₂₅H₄₃NO₃Si
• 分子量: 433.707
• InChiKey: KCYBZWAMJSPVEX-VDKIKQQVSA-N

物化性质

• 沸点：
  479.9±55.0 °C(Predicted)
• 密度：
  0.981±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  41.93
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R)-1-[(3S,5R)-3-allyl-2-benzyl-3-isobutylisoxazolidin-5-yl]-2-(tert-butyldimethylsilanyloxy)ethanol 在 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 作用下， 以 四氢呋喃 、 乙腈 、 叔丁醇 为溶剂， 反应 7.0h， 生成 {(3R,5R)-2-Benzyl-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-3-isobutyl-isoxazolidin-3-yl}-acetaldehyde
  参考文献：
  名称：

  Stereochemical Promiscuity in Artificial Transcriptional Activators

  摘要：

  Small molecule replacements of transcriptional activation domains are highly desirable targets due to their utility as mechanistic tools and their long-term therapeutic potential for a variety of human diseases. Here, we examine the ability of amphipathic isoxazolidines differing only in the placement of constituent side chains to function as transcriptional activation domains. The results reveal that precise positioning of functional groups within a conformationally constrained small molecule scaffold is not required for transcription function; rather, the balance of polarity and hydrophobicity within the scaffold is the more important determinant of transcription function. This suggests that a number of different organic molecule scaffolds should function as transcriptional activator domains when appropriately functionalized, a hypothesis currently under investigation.

  DOI：

  10.1021/ja0536567
• 作为产物：
  描述：

  (1R)-1-[(3S,5R)-3-allyl-3-isobutylisoxazolidin-5-yl]-2-(tert-butyldimethylsilanyloxy)ethanol 、 溴甲苯 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.03h， 以77%的产率得到(1R)-1-[(3S,5R)-3-allyl-2-benzyl-3-isobutylisoxazolidin-5-yl]-2-(tert-butyldimethylsilanyloxy)ethanol
  参考文献：
  名称：

  Stereochemical Promiscuity in Artificial Transcriptional Activators

  摘要：

  Small molecule replacements of transcriptional activation domains are highly desirable targets due to their utility as mechanistic tools and their long-term therapeutic potential for a variety of human diseases. Here, we examine the ability of amphipathic isoxazolidines differing only in the placement of constituent side chains to function as transcriptional activation domains. The results reveal that precise positioning of functional groups within a conformationally constrained small molecule scaffold is not required for transcription function; rather, the balance of polarity and hydrophobicity within the scaffold is the more important determinant of transcription function. This suggests that a number of different organic molecule scaffolds should function as transcriptional activator domains when appropriately functionalized, a hypothesis currently under investigation.

  DOI：

  10.1021/ja0536567