ethyl (R)-2-((3aS,4R,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-fluoroacetate | 132470-46-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (R)-2-((3aS,4R,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-fluoroacetate
• CAS: 132470-46-3
• 化学式: C₁₆H₂₅FO₈
• 分子量: 364.368
• InChiKey: SPVKZLKXIZZIFR-OTNOLWDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.65
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  溴氟乙酸乙酯 、 2,3:5,6-二-O-异亚丙基-D-甘露糖酸-1,4-内酯 在 indium 、 水 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以49%的产率得到ethyl (R)-2-((3aS,4R,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-fluoroacetate
  参考文献：
  名称：

  Studies on indium-mediated additions to lactones: synthesis of 2-deoxy-2-substituted-3-ulosonic acids

  摘要：

  The indium-mediated Reformatsky reaction of a mannose-derived lactone with alpha,alpha-disubstituted-alpha-bromo esters yielded the corresponding ulosonic acid esters as mixtures of anomers. In contrast, the reaction with alpha-monosubstituted-alpha-bromo esters is highly stereoselective and afforded a single anomer of the corresponding (2S)-ulosonic acid esters. A mechanistic proposal for the reaction and an explanation of its outcome is discussed. The indium-mediated Reformatslcy reaction of the mannose-derived lactone with 2-bromo-lactones was also achieved and the products obtained were consistent with those of our proposed mechanism in all cases. Moreover, indium-mediated allylation of the model sugar lactone was also investigated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.011