1-Desoxy-1,1,1-trifluoro-3,4-O-isopropylidene-α-D-ribo-2-hexulofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Desoxy-1,1,1-trifluoro-3,4-O-isopropylidene-α-D-ribo-2-hexulofuranose
• 英文别名: (3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-4-(trifluoromethyl)-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ol
• 化学式: C₉H₁₃F₃O₅
• 分子量: 258.194
• InChiKey: FYHLUOXECMLNNG-UAKXSSHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 在 四乙基氟化铵水合物 作用下， 以 四氢呋喃 为溶剂， 反应 0.42h， 生成 1-Desoxy-1,1,1-trifluoro-3,4-O-isopropylidene-α-D-ribo-2-hexulofuranose
  参考文献：
  名称：

  Synthese Des 5-Desoxy-5,5,5-Trifluoro-d- et -l-Pentofuranoses

  摘要：

  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.

  DOI：

  10.1080/07328309608005689

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.