(1'S,3R,4S,5S)-5-<1'-<1'-(tert-butyldimethylsiloxy)-2',2',2'-trifluoroethyl>>-3,4-dihydroxydihydro-2(3H)-furanone | 149902-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1'S,3R,4S,5S)-5-<1'-<1'-(tert-butyldimethylsiloxy)-2',2',2'-trifluoroethyl>>-3,4-dihydroxydihydro-2(3H)-furanone
• CAS: 149902-86-3
• 化学式: C₁₂H₂₁F₃O₅Si
• 分子量: 330.376
• InChiKey: KTZWDSBZIRZBQZ-KZVJFYERSA-N

物化性质

• 沸点：
  336.3±37.0 °C(predicted)
• 密度：
  1.254±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1'S,3R,4S,5S)-5-<1'-<1'-(tert-butyldimethylsiloxy)-2',2',2'-trifluoroethyl>>-3,4-dihydroxydihydro-2(3H)-furanone 在 硫酸 、 二异丁基氢化铝 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 5-O-(tert-butyldimethylsilyl)-6-deoxy-6,6,6-trifluoro-2,3-O-isopropylidene-D-allo-hexofuranose
  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-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2,2,2-trifluoro-ethyl]-5-trimethylsilanyl-furan 在 18-冠醚-6 potassium permanganate 、 溶剂黄146 作用下， 生成 (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：

  Preparation of 6-deoxy-6,6,6-trifluoro-D-mannose and D-allose from enzymatically resolved 2-butenolides

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)80154-8