(2R,3R)-2-((Z)-3,6-bistrimethylsilanylhex-2-en-5-ynyl)-2-trimethylsilanyltetrahydropyran-3-ol | 1221235-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2R,3R)-2-((Z)-3,6-bistrimethylsilanylhex-2-en-5-ynyl)-2-trimethylsilanyltetrahydropyran-3-ol
• 英文别名: (2R,3R)-2-[(Z)-3,6-bis(trimethylsilyl)hex-2-en-5-ynyl]-2-trimethylsilyloxan-3-ol
• CAS: 1221235-01-3
• 化学式: C₂₀H₄₀O₂Si₃
• 分子量: 396.793
• InChiKey: BTVCXADIHIKMNC-LIVSTFBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-((Z)-3,6-bistrimethylsilanylhex-2-en-5-ynyl)-2-trimethylsilanyltetrahydropyran-3-ol 在 二异丁基氢化铝 、 碘 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 27.0h， 以51%的产率得到(2R,3R)-2-((2Z,5E)-6-iodo-3,6-bistrimethylsilanylhexa-2,5-dienyl)-2-trimethylsilanyltetrahydropyran-3-ol
  参考文献：
  名称：

  Ladder Polyether Synthesis via Epoxide-Opening Cascades Directed by a Disappearing Trimethylsilyl Group

  摘要：

  Epoxide-opening cascades offer the potential to construct complex polyether natural products expeditiously and in a manner that emulates the biogenesis proposed for these compounds. Herein we provide a full account of our development of a strategy that addresses several important challenges of such cascades. The centerpiece of the method is a trimethylsilyl (SiMe3) group that serves several purposes and leaves no trace of itself by the time the cascade has come to an end. The main function of the SiMe3 group is to dictate the regioselectivity of epoxide opening. This strategy is the only general method of effecting endo-selective cascades under basic conditions.

  DOI：

  10.1021/jo1002455
• 作为产物：
  描述：

  1-(三甲基硅基)丙炔 、 (2R,3R)-2-[(E)-3-iodo-3-trimethylsilanylallyl]-2-trimethylsilanyltetrahydropyran-3-ol 在 正丁基锂 、 四甲基乙二胺 、 4-二甲氨基吡啶 、 copper(l) iodide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.75h， 以42%的产率得到(2R,3R)-2-((Z)-3,6-bistrimethylsilanylhex-2-en-5-ynyl)-2-trimethylsilanyltetrahydropyran-3-ol
  参考文献：
  名称：

  Ladder Polyether Synthesis via Epoxide-Opening Cascades Directed by a Disappearing Trimethylsilyl Group

  摘要：

  Epoxide-opening cascades offer the potential to construct complex polyether natural products expeditiously and in a manner that emulates the biogenesis proposed for these compounds. Herein we provide a full account of our development of a strategy that addresses several important challenges of such cascades. The centerpiece of the method is a trimethylsilyl (SiMe3) group that serves several purposes and leaves no trace of itself by the time the cascade has come to an end. The main function of the SiMe3 group is to dictate the regioselectivity of epoxide opening. This strategy is the only general method of effecting endo-selective cascades under basic conditions.

  DOI：

  10.1021/jo1002455

文献信息

• Ladder Polyether Synthesis via Epoxide-Opening Cascades Directed by a Disappearing Trimethylsilyl Group
  作者：Timothy P. Heffron、Graham L. Simpson、Estibaliz Merino、Timothy F. Jamison

  DOI：10.1021/jo1002455

  日期：2010.4.16

  Epoxide-opening cascades offer the potential to construct complex polyether natural products expeditiously and in a manner that emulates the biogenesis proposed for these compounds. Herein we provide a full account of our development of a strategy that addresses several important challenges of such cascades. The centerpiece of the method is a trimethylsilyl (SiMe3) group that serves several purposes and leaves no trace of itself by the time the cascade has come to an end. The main function of the SiMe3 group is to dictate the regioselectivity of epoxide opening. This strategy is the only general method of effecting endo-selective cascades under basic conditions.