(1'S)-2-<1'-(tert-butyldimethylsiloxy)-2',2',2'-trifluoroethyl>-5-(tert-butyldimethylsilyl)furan | 149939-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (1'S)-2-<1'-(tert-butyldimethylsiloxy)-2',2',2'-trifluoroethyl>-5-(tert-butyldimethylsilyl)furan
• CAS: 149939-06-0
• 化学式: C₁₈H₃₃F₃O₂Si₂
• 分子量: 394.625
• InChiKey: YXMZIKNDGQRZRJ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.62
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  22.37
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1'S)-2-<1'-(tert-butyldimethylsiloxy)-2',2',2'-trifluoroethyl>-5-(tert-butyldimethylsilyl)furan 在 palladium on activated charcoal molecular sieve 、 四丁基氟化铵 、 氢气 、 magnesium monoperoxyphthalate hexahydrate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 氯仿 为溶剂， 反应 30.0h， 生成 (1'S,5R)-5-<1'-(2',2',2'-trifluoro-1-hydroxyethyl)>dihydro-2(3H)-furanone
  参考文献：
  名称：

  Development of a novel pathway to access 6-deoxy-6,6,6-trifluoro sugars via 1,2-migration of a tert-butyldimethylsilyl group

  摘要：

  Trifluoromethylated furanols 2 were enzymatically resolved into the corresponding optically active forms in a highly efficient manner and were further converted to the synthetically useful 2-butenolides 6. Introduction of substituents into these butenolides 6 or their saturated lactone forms 8 was realized by boron trifluoride-mediated Michael addition of cuprates or by capture of the enolates with various kinds of electrophiles, respectively, both of which proceeded with a high degree of diastereoselectivity. Moreover, novel synthetic routes to access 6-deoxy-6,6,6-trifluorosugars were developed by the utilization of 1,2-silyl migration as a key step, which was qualitatively supported by PM3 molecular orbital calculation.

  DOI：

  10.1021/jo00068a033
• 作为产物：
  描述：

  2-(tert-butyldimethylsilyl)-5-(trifluoroacetyl)furan 在 吡啶 、 咪唑 、 sodium tetrahydroborate 、 水 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (1'S)-2-<1'-(tert-butyldimethylsiloxy)-2',2',2'-trifluoroethyl>-5-(tert-butyldimethylsilyl)furan
  参考文献：
  名称：

  Development of a novel pathway to access 6-deoxy-6,6,6-trifluoro sugars via 1,2-migration of a tert-butyldimethylsilyl group

  摘要：

  Trifluoromethylated furanols 2 were enzymatically resolved into the corresponding optically active forms in a highly efficient manner and were further converted to the synthetically useful 2-butenolides 6. Introduction of substituents into these butenolides 6 or their saturated lactone forms 8 was realized by boron trifluoride-mediated Michael addition of cuprates or by capture of the enolates with various kinds of electrophiles, respectively, both of which proceeded with a high degree of diastereoselectivity. Moreover, novel synthetic routes to access 6-deoxy-6,6,6-trifluorosugars were developed by the utilization of 1,2-silyl migration as a key step, which was qualitatively supported by PM3 molecular orbital calculation.

  DOI：

  10.1021/jo00068a033