[(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 | 634189-22-3

• 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] 2-[(1R,2S)-2-hydroxycyclopentyl]acetate
• CAS: 634189-22-3
• 化学式: C₂₀H₂₆O₆
• 分子量: 362.423
• InChiKey: DZHUVXSWMWHIIY-ZHRPLEGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 [(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 在 氢氧化钾 、 硫酸 作用下， 以 甲醇 为溶剂， 生成 (+/-)-methyl trans-2-hydroxy-cyclopentane-1-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 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 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] 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