(4R,5R)-2,2-Dimethyl-5-((S)-2,2,2-trifluoro-1-methoxymethoxy-ethyl)-[1,3]dioxolane-4-carbaldehyde | 182346-29-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-2,2-Dimethyl-5-((S)-2,2,2-trifluoro-1-methoxymethoxy-ethyl)-[1,3]dioxolane-4-carbaldehyde
• CAS: 182346-29-8
• 化学式: C₁₀H₁₅F₃O₅
• 分子量: 272.221
• InChiKey: OBSRUHQZNBHVPV-RNJXMRFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4R,5R)-2,2-Dimethyl-5-((S)-2,2,2-trifluoro-1-methoxymethoxy-ethyl)-[1,3]dioxolane-4-carbaldehyde 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3R,4R,5S)-5-Trifluoromethyl-tetrahydro-furan-2,3,4-triol 、 (2R,3R,4R,5S)-5-Trifluoromethyl-tetrahydro-furan-2,3,4-triol
  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
• 作为产物：
  描述：

  (4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane 在 palladium on activated charcoal 草酰氯 、 氢气 、 sodium hydride 、 四乙基氟化铵水合物 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， -60.0~25.0 ℃ 、100.0 kPa 条件下， 反应 0.92h， 生成 (4R,5R)-2,2-Dimethyl-5-((S)-2,2,2-trifluoro-1-methoxymethoxy-ethyl)-[1,3]dioxolane-4-carbaldehyde
  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