5-methyl-2,5-bis-trimethylsilanyl-octahydro-[2,2']bifuranyl-4-ol | 877384-29-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 5-methyl-2,5-bis-trimethylsilanyl-octahydro-[2,2']bifuranyl-4-ol
• 英文别名: (2S,4R,5R,2'S)-5-methyl-2,5-bistrimethylsilanyloctahydro-[2,2']bifuranyl-4-ol
• CAS: 877384-29-7
• 化学式: C₁₅H₃₂O₃Si₂
• 分子量: 316.588
• InChiKey: YZGCULGQGWWPLG-ZQDZILKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-methyl-2,5-bis-trimethylsilanyl-octahydro-[2,2']bifuranyl-4-ol 、 乙酸酐 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到acetic acid 5-methyl-2,5-bis-trimethylsilanyl-octahydro-[2,2']bifuranyl-4-yl ester
  参考文献：
  名称：

  Ladder Polyether Synthesis via Epoxide-Opening Cascades Using a Disappearing Directing Group

  摘要：

  The combination of a trimethylsilyl group, a Brønsted base, a fluoride source, and a hydroxylic solvent enables the first construction of the tetrad of tetrahydropyran rings found in the majority of the ladder polyether natural products by way of a cascade of epoxide-opening events that emulates the final step of Nakanishi's proposed biosynthetic pathway. The trimethylsilyl group disappears during the course of the cascade, and thus these are the first epoxide ring-opening cascades that afford ladder polyether subunits containing no directing groups at the end of the cascade.

  DOI：

  10.1021/ja057973p
• 作为产物：
  描述：

  3-[(2R,3S)-3-((2R,3S)-3-methyl-3-silanyloxiranylmethyl)-3-silanyloxiranyl]propan-1-ol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以50%的产率得到5-methyl-2,5-bis-trimethylsilanyl-octahydro-[2,2']bifuranyl-4-ol
  参考文献：
  名称：

  Ladder Polyether Synthesis via Epoxide-Opening Cascades Using a Disappearing Directing Group

  摘要：

  The combination of a trimethylsilyl group, a Brønsted base, a fluoride source, and a hydroxylic solvent enables the first construction of the tetrad of tetrahydropyran rings found in the majority of the ladder polyether natural products by way of a cascade of epoxide-opening events that emulates the final step of Nakanishi's proposed biosynthetic pathway. The trimethylsilyl group disappears during the course of the cascade, and thus these are the first epoxide ring-opening cascades that afford ladder polyether subunits containing no directing groups at the end of the cascade.

  DOI：

  10.1021/ja057973p

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.