5-Desoxy-5,5,5-trifluoro-2,3-O-isopropylidene-L-lyxonolactone | 154673-27-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Desoxy-5,5,5-trifluoro-2,3-O-isopropylidene-L-lyxonolactone
• CAS: 154673-27-5
• 化学式: C₈H₉F₃O₄
• 分子量: 226.152
• InChiKey: WMVOUUOXZAIMKK-VPENINKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-Desoxy-5,5,5-trifluoro-2,3-O-isopropylidene-L-lyxonolactone 在 lithium aluminium tetrahydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 12.0h， 生成 1-Desoxy-1,1,1-trifluoro-3,4-O-isopropylidene-L-arabinitol
  参考文献：
  名称：

  Trifluoromethylation of sugar 1,4-lactones : Synthesis of 5-deoxy-5,5,5-trifluoro-D and L-ribose and lyxose derivatives

  摘要：

  The four 5-deoxy-5,5,5-trifluoro-D and L-ribo and -lyxo furanoses were synthesized from lactones using CF(3)SiMe(3) in 5 or 6 steps and 30-40 % overall yield. The key step was a stereoselective reduction of 1,1,1-trifluoror-2-ketoses with LialH(4) or NaBH4 at an anomeric centre.

  DOI：

  10.1016/s0040-4039(00)61400-4
• 作为产物：
  描述：

  1-Desoxy-1,1,1-trifluoro-3,4-O-isopropylidene-L-erythrulose 在 lithium aluminium tetrahydride 、 重铬酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.42h， 生成 5-Desoxy-5,5,5-trifluoro-2,3-O-isopropylidene-L-lyxonolactone
  参考文献：
  名称：

  Trifluoromethylation of sugar 1,4-lactones : Synthesis of 5-deoxy-5,5,5-trifluoro-D and L-ribose and lyxose derivatives

  摘要：

  The four 5-deoxy-5,5,5-trifluoro-D and L-ribo and -lyxo furanoses were synthesized from lactones using CF(3)SiMe(3) in 5 or 6 steps and 30-40 % overall yield. The key step was a stereoselective reduction of 1,1,1-trifluoror-2-ketoses with LialH(4) or NaBH4 at an anomeric centre.

  DOI：

  10.1016/s0040-4039(00)61400-4

文献信息

• Synthese Des 5-Desoxy-5,5,5-Trifluoro-d- et -l-Pentofuranoses
  作者：Pascal Munier、Marie-Béatrice Giudicelli、Dominique Picq、Daniel Anker

  DOI：10.1080/07328309608005689

  日期：1996.8

  Synthetic pathways leading to 5-deoxy-5,5,5-trifluoropentofuranoses are reported. The main difficulty was to obtain a good diastereoselectivity at the C-4 carbon bearing the CF3 group. For the ribose and the lyxose derivatives the problem was partially solved by reacting trifluoromethyltrimethylsilane with 1,4-lactones of suitable glyconic acids leading to hemiketalic 1-deoxy-1,1,1-trifluoro-2-ketoses. Reduction of these ketoses with NaBH4 or LiAlH4 allowed the desired configuration at the C-4 carbon. For the arabinose and the xylose derivatives it was found more convenient to synthesize uncyclised 1-deoxy-1,1,1-trifluoro-2-ketopentoses by Dess-Martin oxidation of the corresponding protected alcohols. Highly selective reductions of these trifluoromethylketones led to arabino or xylo derivatives depending on the reducing agent.