(3S,5R)-3-benzyl-5[(1R)-1,2-bis(tert-butyldimethylsilanyloxy)ethyl]-3-isobutylisoxazolidine | 866483-46-7

• 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: (3S,5R)-3-benzyl-5[(1R)-1,2-bis(tert-butyldimethylsilanyloxy)ethyl]-3-isobutylisoxazolidine
• 英文别名: [(1R)-1-[(3S,5R)-3-benzyl-3-(2-methylpropyl)-1,2-oxazolidin-5-yl]-2-[tert-butyl(dimethyl)silyl]oxyethoxy]-tert-butyl-dimethylsilane
• CAS: 866483-46-7
• 化学式: C₂₈H₅₃NO₃Si₂
• 分子量: 507.905
• InChiKey: OWDATTJUOYRTFR-SKVJQKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.72
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,5R)-3-benzyl-5[(1R)-1,2-bis(tert-butyldimethylsilanyloxy)ethyl]-3-isobutylisoxazolidine 在 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 12.07h， 生成
  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：

  2-(tert-butyldimethylsilanyloxy)-(1R)-1-[(5R)-3-isobutyl-4,5-dihydroisoxazol-5-yl]-ethanol 在 4-二甲氨基吡啶 、 三氟化硼乙醚 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (3S,5R)-3-benzyl-5[(1R)-1,2-bis(tert-butyldimethylsilanyloxy)ethyl]-3-isobutylisoxazolidine
  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

文献信息

• A flexible synthetic route to isoxazolidine β-proline analogs
  作者：Sara J. Buhrlage、Bin Chen、Anna K. Mapp

  DOI：10.1016/j.tet.2008.12.062

  日期：2009.4

  relatively unexplored compared to other foldamer classes due in part to synthetic challenges associated with substituted monomers. Here we report a flexible synthesis of di- and trisubstituted isoxazolidine β-proline monomers that enables access to a wide range of densely functionalized analogs suitably protected for solid-phase synthetic protocols. This strategy utilizes chiral isoxazolines as key intermediates

  与其他折叠剂类别相比，β-脯氨酸低聚物的功能和高级结构尚未得到充分研究，部分原因是与取代单体有关的合成挑战。在这里，我们报告了二和三取代的异恶唑烷β-脯氨酸单体的灵活合成方法，该方法能够获得各种适用于固相合成方案的稠密官能化类似物。该策略利用手性异恶唑啉作为关键中间体，可以轻松提供目标分子的单一立体异构体。