(1'S,4S)-4-<1'-<1'-(tert-butyldimethylsiloxy)-2',2',2'-trifluoroethyl>>-2-buten-4-olide | 140404-41-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (1'S,4S)-4-<1'-<1'-(tert-butyldimethylsiloxy)-2',2',2'-trifluoroethyl>>-2-buten-4-olide
• CAS: 140404-41-7
• 化学式: C₁₂H₁₉F₃O₃Si
• 分子量: 296.362
• InChiKey: MYHXXPGHTPDKNX-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1'S,4S)-4-<1'-<1'-(tert-butyldimethylsiloxy)-2',2',2'-trifluoroethyl>>-2-buten-4-olide 在 potassium permanganate 、 18-冠醚-6 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以42%的产率得到(1'S,3R,4S,5S)-5-<1'-<1'-(tert-butyldimethylsiloxy)-2',2',2'-trifluoroethyl>>-3,4-dihydroxydihydro-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：

  (1'S)-2-<1'-(2',2',2'-trifluoro-1'-hydroxyethyl)>-5-(trimethylsilyl)furan 在 咪唑 、 magnesium monoperoxyphthalate hexahydrate 、 溶剂黄146 作用下， 生成 (1'S,4S)-4-<1'-<1'-(tert-butyldimethylsiloxy)-2',2',2'-trifluoroethyl>>-2-buten-4-olide
  参考文献：
  名称：

  Chiral trifluoromethylated 2-butenolides for the construction of 6-deoxy-6,6,6-trifluorosugars

  摘要：

  带有三氟甲基（CF3）基团的具有光学活性的 2-丁烯酸酯是通过酶促光学解析法合成的，并通过碱促进叔丁基二甲基硅基的 1,2 迁移高效地选择性转化为 6,6,6- 三氟十二烷糖和二十二烷糖。

  DOI：

  10.1039/c39920000055

文献信息

• Preparation of 6-deoxy-6,6,6-trifluoro-D-mannose and D-allose from enzymatically resolved 2-butenolides
  作者：Takashi Yamazaki、Kenji Mizutani、Tomoya Kitazume

  DOI：10.1016/s0957-4166(00)80154-8

  日期：1993.5

  Both 6-deoxy-6,6,6-trifluoro-D-mannose and D-allose, possessing a diastereomeric relationship, were conveniently prepared from trifluorinated 2-butenolides, which was prepared via the enzymatic resolution with high efficiency.