4-O-(tert-butyldimethylsilyl)-2,3,6-trideoxy-6,6,6-trifluoro-L-gluco-hexopyranose | 287736-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 4-O-(tert-butyldimethylsilyl)-2,3,6-trideoxy-6,6,6-trifluoro-L-gluco-hexopyranose
• 英文别名: (5R,6R)-5-[tert-butyl(dimethyl)silyl]oxy-6-(trifluoromethyl)oxan-2-ol
• CAS: 287736-07-6
• 化学式: C₁₂H₂₃F₃O₃Si
• 分子量: 300.394
• InChiKey: FNIKQKLRTIMGRY-RCAUJQPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-O-(tert-butyldimethylsilyl)-2,3,6-trideoxy-6,6,6-trifluoro-L-gluco-hexopyranose 在 吡啶 、 四丁基氟化铵 、 对甲苯磺酸 作用下， 生成 4'-Hexyloxy-biphenyl-4-carboxylic acid (2R,3R,6S)-6-hexyloxy-2-trifluoromethyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis and Properties of Pyranose Derivatives with Trifluoromethyl Group Used as Chiral Dopants for Ferroelectric Liquid Crystals

  摘要：

  合成了多种带有三氟甲基的吡喃糖衍生物，发现它们是铁电液晶的优异手性掺杂剂。讨论了分子结构与诱导铁电性质之间的关系。

  DOI：

  10.1246/cl.1994.839
• 作为产物：
  描述：

  5-O-(tert-butyldimethylsilyl)-2,3,6-trideoxy-6,6,6-trifluoro-L-gluco-hexofuranose 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 4-O-(tert-butyldimethylsilyl)-2,3,6-trideoxy-6,6,6-trifluoro-L-gluco-hexopyranose
  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

• Development of a novel pathway to access 6-deoxy-6,6,6-trifluoro sugars via 1,2-migration of a tert-butyldimethylsilyl group
  作者：Takashi Yamazaki、Kenji Mizutani、Tomoya Kitazume

  DOI：10.1021/jo00068a033

  日期：1993.7

  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.