(R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2,3,3,4,4,5,5,5-nonafluoro-pentan-1-ol | 204315-92-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2,3,3,4,4,5,5,5-nonafluoro-pentan-1-ol
• 英文别名: (1R)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2,2,3,3,4,4,5,5,5-nonafluoropentan-1-ol
• CAS: 204315-92-4
• 化学式: C₁₉H₁₉F₉O₅
• 分子量: 498.342
• InChiKey: OBKDKVBLKIRXRN-ODXJTPSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2,3,3,4,4,5,5,5-nonafluoro-pentan-1-ol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 96.0h， 以90%的产率得到(3aR,5S,6S,6aR)-2,2-Dimethyl-5-((R)-2,2,3,3,4,4,5,5,5-nonafluoro-1-hydroxy-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol
  参考文献：
  名称：

  Organofluorine Compounds and Fluorinating Agents; 20: The Nucleophilic Perfluoroalkylation of Sugar Aldehydes Using a Sonochemical Barbier-Type Reaction

  摘要：

  DOI：

  10.1055/s-1998-2101
• 作为产物：
  描述：

  全氟碘代丁烷 、 3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖 在 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以17%的产率得到(S)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2,3,3,4,4,5,5,5-nonafluoro-pentan-1-ol
  参考文献：
  名称：

  Organofluorine Compounds and Fluorinating Agents; 20: The Nucleophilic Perfluoroalkylation of Sugar Aldehydes Using a Sonochemical Barbier-Type Reaction

  摘要：

  DOI：

  10.1055/s-1998-2101

文献信息

• Stereoselectivity of the nucleophilic F-alkylation of carbonylated carbohydrates
  作者：Sandrine Lavaire、Richard Plantier-Royon、Charles Portella

  DOI：10.1016/s0957-4166(97)00620-4

  日期：1998.1

  The addition of F-alkyl organometallics to carbonylated carbohydrates 1-3 was carried out using trimethylsilyl or bromomagnesium reagents. The results are strongly dependent upon both the nature of the metal and of the substrate. Compounds 1 and 2 were transformed with high stereoselectivity into the L-ido adduct using F-organomagnesium reagents, whereas the D-allo adduct was obtained with complete stereoselectivity using fluoride activated addition of F-organosilanes on compound 3. Comparison with literature data emphasizes the enhanced stereoselectivity exhibited by perfluoroorgoanometallic reagents. The difference between the stereoselectivity of the addition of magnesium versus silyl reagents was attributed to chelation effects. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Organofluorine Compounds and Fluorinating Agents; 20: The Nucleophilic Perfluoroalkylation of Sugar Aldehydes Using a Sonochemical Barbier-Type Reaction
  作者：Dietmar Peters

  DOI：10.1055/s-1998-2101

  日期：1998.7