(1R,5R,8S)-8-formyl-6-O-β-methyl-4-methylene-2,7-dioxabicyclo<3.3.0>octane

• 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: (1R,5R,8S)-8-formyl-6-O-β-methyl-4-methylene-2,7-dioxabicyclo<3.3.0>octane
• 英文别名: (3aS,4R,6S,6aR)-4-methoxy-3-methylidene-3a,4,6,6a-tetrahydrofuro[3,4-b]furan-6-carbaldehyde
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: CRSXUAYPYPNNAR-RYPBNFRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙基溴化镁 、 (1R,5R,8S)-8-formyl-6-O-β-methyl-4-methylene-2,7-dioxabicyclo<3.3.0>octane 以 四氢呋喃 为溶剂， 反应 4.0h， 以76%的产率得到(1R,5S,8S)-8-(1'RS-hydroxybutyl)-6-O-β-methyl-4-methylene-2,7-dioxabicyclo<3.3.0>octane
  参考文献：
  名称：

  Radical reactions on furanoside acetals: A formal synthesis of (−)-canadensolide from D-mannose

  摘要：

  By adaption of an intramolecular radical cyclisation protocol to the furanoid glycal derivative 3 derived from D-mannose, synthesis of the crucial bicyclo[3.3.0]octane system 6 is reported. A sequence of reactions on this key synthon 6, leading to the formal synthesis of (-)-canadensolide (1) is described.

  DOI：

  10.1016/0957-4166(95)00038-q
• 作为产物：
  描述：

  (R)-1-((3aS,4R,6R,6aR)-4-Methoxy-3-methylene-hexahydro-furo[3,4-b]furan-6-yl)-ethane-1,2-diol 在 sodium periodate 、 水 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以68%的产率得到(1R,5R,8S)-8-formyl-6-O-β-methyl-4-methylene-2,7-dioxabicyclo<3.3.0>octane
  参考文献：
  名称：

  Radical reactions on furanoside acetals: A formal synthesis of (−)-canadensolide from D-mannose

  摘要：

  By adaption of an intramolecular radical cyclisation protocol to the furanoid glycal derivative 3 derived from D-mannose, synthesis of the crucial bicyclo[3.3.0]octane system 6 is reported. A sequence of reactions on this key synthon 6, leading to the formal synthesis of (-)-canadensolide (1) is described.

  DOI：

  10.1016/0957-4166(95)00038-q

文献信息

• Radical reactions on furanoside acetals: A formal synthesis of (−)-canadensolide from D-mannose
  作者：GVM Sharma、Kasireddy Krishnudu、S Mahender Rao

  DOI：10.1016/0957-4166(95)00038-q

  日期：1995.2

  By adaption of an intramolecular radical cyclisation protocol to the furanoid glycal derivative 3 derived from D-mannose, synthesis of the crucial bicyclo[3.3.0]octane system 6 is reported. A sequence of reactions on this key synthon 6, leading to the formal synthesis of (-)-canadensolide (1) is described.