(1R,5S,8R)-8-(1'-butanyl)-6-O-β-methyl-4-methylene-2,7-dioxabicyclo<3.3.0>octane | 133577-16-9

• 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,5S,8R)-8-(1'-butanyl)-6-O-β-methyl-4-methylene-2,7-dioxabicyclo<3.3.0>octane
• 英文别名: (3aS,4R,6R,6aR)-6-butyl-4-methoxy-3-methylidene-3a,4,6,6a-tetrahydrofuro[3,4-b]furan
• CAS: 133577-16-9
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: VNBGWLHVXITCCP-NOOOWODRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,5S,8R)-8-(1'-butanyl)-6-O-β-methyl-4-methylene-2,7-dioxabicyclo<3.3.0>octane 在 吡啶 、 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以74%的产率得到methyl-2-C-(carboxymethylenemethyl)-2,5-dideoxy-5-C-(n-propyl)-D-lyxofuranoside-2,3-γ-lactone
  参考文献：
  名称：

  Stereoselective synthesis of (−)-canadensolide from D-glucose

  摘要：

  A simple and stereoselective synthesis of (-)-canadenosolide starting from D-glucose, through a radical mediated cyclisation, has been described.

  DOI：

  10.1016/s0040-4020(01)90507-1
• 作为产物：
  描述：

  (3aS,6R,6aR)-6-butyl-4-methoxy-3-methylidene-3a,4,6,6a-tetrahydrofuro[3,4-b]furan 生成 (1R,5S,8R)-8-(1'-butanyl)-6-O-β-methyl-4-methylene-2,7-dioxabicyclo<3.3.0>octane
  参考文献：
  名称：

  SHARMA, G. V. M.;VEPACHEDU, SPEENIVASA RAO, TETRAHEDRON, 47,(1991) N, C. 519-524

  摘要：

  DOI：

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.
• SHARMA, G. V. M.;VEPACHEDU, SPEENIVASA RAO, TETRAHEDRON, 47,(1991) N, C. 519-524
  作者：SHARMA, G. V. M.、VEPACHEDU, SPEENIVASA RAO

  DOI：——

  日期：——
• Stereoselective synthesis of (−)-canadensolide from D-glucose
  作者：GVM Sharma、Vepachedu Sreenivasa Rao

  DOI：10.1016/s0040-4020(01)90507-1

  日期：1991.1

  A simple and stereoselective synthesis of (-)-canadenosolide starting from D-glucose, through a radical mediated cyclisation, has been described.