(-)-(1R,2S,3S,4R)-3-Hydroxy-4-(2'-hydroxyethyl)-1,2-isopropylidenedioxycyclopentane | 145741-51-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(1R,2S,3S,4R)-3-Hydroxy-4-(2'-hydroxyethyl)-1,2-isopropylidenedioxycyclopentane
• 英文别名: (3aS,4S,5R,6aR)-5-(2-hydroxyethyl)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
• CAS: 145741-51-1
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: LTBUEDVFOMMVMQ-LURQLKTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(1R,2S,3S,4R)-3-Hydroxy-4-(2'-hydroxyethyl)-1,2-isopropylidenedioxycyclopentane 在 Amberlyst 15 (H+) 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以92%的产率得到(-)-(1R,2R,3S,4R)-4-(2'-Hydroxyethyl)cyclopentane-1,2,3-triol
  参考文献：
  名称：

  Radical cyclisation reactions leading to polyhydroxylated cyclopentane derivatives: synthesis of (1R,2R,3S,4R)- and (1S,2S,3R,4S)-4-hydroxyethylcyclopentane-1,2,3-triol

  摘要：

  The tetraol (-)-1 has been prepared from a derivative of (D)-allose 3. The stereoselective carbocyclization reaction (8 double line arrow pointing right 11) formed the key step in this sequence. The enantiomeric cyclopentane derivative(+)-1 was also prepared from compound 3.In this synthesis the cyclization of compound 18 to provide the carbocycle 19 features as the critical carbon-carbon bond forming reaction.

  DOI：

  10.1039/p19920002625
• 作为产物：
  描述：

  (-)-(1R,2S,3S,4R)-3-Benzyloxy-4-(2'-hydroxyethyl)-1,2-isopropylidenedioxycyclopentane 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 15.5h， 以89%的产率得到(-)-(1R,2S,3S,4R)-3-Hydroxy-4-(2'-hydroxyethyl)-1,2-isopropylidenedioxycyclopentane
  参考文献：
  名称：

  Radical cyclisation reactions leading to polyhydroxylated cyclopentane derivatives: synthesis of (1R,2R,3S,4R)- and (1S,2S,3R,4S)-4-hydroxyethylcyclopentane-1,2,3-triol

  摘要：

  The tetraol (-)-1 has been prepared from a derivative of (D)-allose 3. The stereoselective carbocyclization reaction (8 double line arrow pointing right 11) formed the key step in this sequence. The enantiomeric cyclopentane derivative(+)-1 was also prepared from compound 3.In this synthesis the cyclization of compound 18 to provide the carbocycle 19 features as the critical carbon-carbon bond forming reaction.

  DOI：

  10.1039/p19920002625