[(3R,3aR,6R,6aR)-3-phenylmethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] (E)-7-oxohept-2-enoate | 634189-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: [(3R,3aR,6R,6aR)-3-phenylmethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] (E)-7-oxohept-2-enoate
• CAS: 634189-20-1
• 化学式: C₂₀H₂₄O₆
• 分子量: 360.407
• InChiKey: RDKGXQKXHLLYQZ-AADJAFEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3R,3aR,6R,6aR)-3-phenylmethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] (E)-7-oxohept-2-enoate 在 zinc(II) chloride 三乙基硼 、 氧气 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以93%的产率得到[(3R,3aR,6R,6aR)-3-phenylmethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] 2-[(1R,2S)-2-hydroxycyclopentyl]acetate
  参考文献：
  名称：

  Aldehyde–alkene cyclizations via O-stannyl ketyl radicals using sugars as chiral auxiliaries

  摘要：

  This investigation illustrates the utility of two inexpensive carbohydrate derivatives as sources of asymmetry for aldehyde-alkene radical cyclizations. Diastereomeric ratios as high as 9:1 were achieved with an ester-appended (+)-isosorbide and 100:1 for (+)-isomannide. Temperature dependence, Lewis acids and solvents were all examined. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.006
• 作为产物：
  描述：

  1,4:3,6-dianhydro-D-mannitol 在 吡啶 、 sodium hydroxide 作用下， 反应 12.0h， 生成 [(3R,3aR,6R,6aR)-3-phenylmethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] (E)-7-oxohept-2-enoate
  参考文献：
  名称：

  Aldehyde–alkene cyclizations via O-stannyl ketyl radicals using sugars as chiral auxiliaries

  摘要：

  This investigation illustrates the utility of two inexpensive carbohydrate derivatives as sources of asymmetry for aldehyde-alkene radical cyclizations. Diastereomeric ratios as high as 9:1 were achieved with an ester-appended (+)-isosorbide and 100:1 for (+)-isomannide. Temperature dependence, Lewis acids and solvents were all examined. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.006

文献信息

• Aldehyde–alkene cyclizations via O-stannyl ketyl radicals using sugars as chiral auxiliaries
  作者：Eric J. Enholm、Florent Allais、Sebastian Bareyt

  DOI：10.1016/j.tetasy.2003.07.006

  日期：2003.10

  This investigation illustrates the utility of two inexpensive carbohydrate derivatives as sources of asymmetry for aldehyde-alkene radical cyclizations. Diastereomeric ratios as high as 9:1 were achieved with an ester-appended (+)-isosorbide and 100:1 for (+)-isomannide. Temperature dependence, Lewis acids and solvents were all examined. (C) 2003 Elsevier Ltd. All rights reserved.