(1S,2R,4R,5R)-2-benzyloxy-4-(benzyloxymethyl)-6-oxabicyclo[3.1.0]hexane | 524011-35-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R,4R,5R)-2-benzyloxy-4-(benzyloxymethyl)-6-oxabicyclo[3.1.0]hexane
• 英文别名: (1R,2R,4R,5S)-1-methyl-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-oxabicyclo[3.1.0]hexane
• CAS: 524011-35-6
• 化学式: C₂₁H₂₄O₃
• 分子量: 324.42
• InChiKey: ZVMPXCBEZHHTAB-MXEMCNAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R,4R,5R)-2-benzyloxy-4-(benzyloxymethyl)-6-oxabicyclo[3.1.0]hexane 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 乙醚 、 甲醇 为溶剂， 反应 120.0h， 以93%的产率得到(1S,3R,5R)-5-(羟基甲基)-1-甲基-1,3-环戊烷二醇
  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：

  ethyl cis-4-hydroxy-2-methylcyclopent-2-ene-1-carboxylate 在 lithium aluminium tetrahydride 、 二甲基二环氧乙烷 、 四丁基碘化铵 、 sodium hydride 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 66.0h， 生成 (1S,2R,4R,5R)-2-benzyloxy-4-(benzyloxymethyl)-6-oxabicyclo[3.1.0]hexane
  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

文献信息

• Enantioselective Synthesis of 3-Methylcarbapentofuranose Derivatives, Based on a Chemoenzymatic Procedure
  作者：Gérard Audran、Samir Acherar、Honoré Monti

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

  日期：2003.1

  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.