(S)-4-((2S,4R,5R)-4-hydroxy-5-methyl-2,5-bistrimethylsilanyltetrahydrofuran-2-yl)-[1,3]dioxolan-2-one | 1221235-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (S)-4-((2S,4R,5R)-4-hydroxy-5-methyl-2,5-bistrimethylsilanyltetrahydrofuran-2-yl)-[1,3]dioxolan-2-one
• 英文别名: (4S)-4-[(2S,4R,5R)-4-hydroxy-5-methyl-2,5-bis(trimethylsilyl)oxolan-2-yl]-1,3-dioxolan-2-one
• CAS: 1221235-06-8
• 化学式: C₁₄H₂₈O₅Si₂
• 分子量: 332.544
• InChiKey: LEHBTLSMLLBANH-WVWOOGAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl [3-[(3-methyl-3-trimethylsilyloxiran-2-yl)methyl]-3-trimethylsilyloxiran-2-yl]methyl carbonate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 以36%的产率得到(S)-4-((2S,4R,5R)-4-hydroxy-5-methyl-2,5-bistrimethylsilanyltetrahydrofuran-2-yl)-[1,3]dioxolan-2-one
  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