ethyl (1S,2R,3R,4R)-2,3,4-trihydroxy-2-methylcyclopentane-1-carboxylate | 524011-39-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (1S,2R,3R,4R)-2,3,4-trihydroxy-2-methylcyclopentane-1-carboxylate
• CAS: 524011-39-0
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: ZNOHUFNGMCTPRO-JXOAFFINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 ethyl (1S,2R,3R,4R)-2,3,4-trihydroxy-2-methylcyclopentane-1-carboxylate 在 lithium aluminium tetrahydride 、 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 49.0h， 以86%的产率得到(1R,2R,3R,4R)-3,4-diacetoxy-2-hydroxy-2-methylcyclopentylmethyl acetate
  参考文献：
  名称：

  Enantioselective Synthesis of 3-Methylcarbapentofuranose Derivatives, Based on a Chemoenzymatic Procedure

  摘要：

  The enantioselective synthesis of 3-methylcarbapentofuranose derivatives through the use of a racemic substituted cyclopentenylcarboxylate as the carbon building block and a number of stereoselective transformations is described. All of the stereogenic centres of these derivatives are directed by the two stereogenic centres created early in the key cyclopentene moiety by a lipase-catalysed enantioselective acetylation.

  DOI：

  10.1002/1099-0690(200301)2003:1<92::aid-ejoc92>3.0.co;2-v
• 作为产物：
  描述：

  (1S,2S,4R,5R)-4-hydroxy-1-methyl-6-oxa-bicyclo[3.1.0]hexane-2-carboxylic acid ethyl ester 在 高氯酸 作用下， 以 水 为溶剂， 反应 72.0h， 以91%的产率得到ethyl (1S,2R,3R,4R)-2,3,4-trihydroxy-2-methylcyclopentane-1-carboxylate
  参考文献：
  名称：

  Enantioselective Synthesis of 3-Methylcarbapentofuranose Derivatives, Based on a Chemoenzymatic Procedure

  摘要：

  The enantioselective synthesis of 3-methylcarbapentofuranose derivatives through the use of a racemic substituted cyclopentenylcarboxylate as the carbon building block and a number of stereoselective transformations is described. All of the stereogenic centres of these derivatives are directed by the two stereogenic centres created early in the key cyclopentene moiety by a lipase-catalysed enantioselective acetylation.

  DOI：

  10.1002/1099-0690(200301)2003:1<92::aid-ejoc92>3.0.co;2-v