(2R,5S)-2-<(2S,5R)-5-((1S,4S)-1,4-dihydroxy-1-methylpentyl)tetrahydrofuran-2-yl>tetrahydro-2,5-dimethylfuran | 132298-82-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2R,5S)-2-<(2S,5R)-5-((1S,4S)-1,4-dihydroxy-1-methylpentyl)tetrahydrofuran-2-yl>tetrahydro-2,5-dimethylfuran
• 英文别名: (2S,5S)-2-[(2R,5S)-5-[(2R,5S)-2,5-dimethyloxolan-2-yl]oxolan-2-yl]hexane-2,5-diol
• CAS: 132298-82-9
• 化学式: C₁₆H₃₀O₄
• 分子量: 286.412
• InChiKey: WEJSEMGUYMOPDW-KXKVQDCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  5
• 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：

  (2R,5S)-2-<(2S,5R)-5-((1S,4S)-1,4-dihydroxy-1-methylpentyl)tetrahydrofuran-2-yl>tetrahydro-2,5-dimethylfuran 在 吡啶 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以78%的产率得到(2R*,5S*)-tetrahydro-2-<(2S*,5R*)-tetrahydro-5-((2S*,5R*)-tetrahydro-2,5-dimethylfuran-2-yl)furan-2-yl>-2,5-dimethylfuran
  参考文献：
  名称：

  Total synthesis of the meso-triterpene polyether teurilene

  摘要：

  The first total synthesis of the triterpene ether teurilene (1) has been accomplished utilizing two vanadium(V)-catalyzed oxidation-cyclization reactions with different stereoselectivities. The synthesis involved stereoselective and step-by-step construction of 2,5-cis- and 2,5-trans-tetrahydrofuran rings, vanadium(V)-catalyzed oxidation of 4-substituted 4-en-1-ol 40 and subsequent cyclization of the resulting anti-epoxy alcohol 41, and a similar oxidation-cyclization of 5-substituted 4-en-1-ol 49 by way of syn-epoxy alcohol 50. This was followed by construction of a third tetrahydrofuran ring by more conventional means. An improved synthesis of 1, which featured direct formation of bis(tetrahydrofuran) 51 from squalene derivative 66 by simultaneous double oxidation-cyclization, was also accomplished.

  DOI：

  10.1021/jo00007a013
• 作为产物：
  描述：

  (2S,5E,9E,13S)-13-(Benzoyloxy)-5,10-dimethyltetradeca-5,9-dien-2-ol 在 bis(acetylacetonate)oxovanadium 叔丁基过氧化氢 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (2R,5S)-2-<(2S,5R)-5-((1S,4S)-1,4-dihydroxy-1-methylpentyl)tetrahydrofuran-2-yl>tetrahydro-2,5-dimethylfuran
  参考文献：
  名称：

  Total synthesis of the meso-triterpene polyether teurilene

  摘要：

  The first total synthesis of the triterpene ether teurilene (1) has been accomplished utilizing two vanadium(V)-catalyzed oxidation-cyclization reactions with different stereoselectivities. The synthesis involved stereoselective and step-by-step construction of 2,5-cis- and 2,5-trans-tetrahydrofuran rings, vanadium(V)-catalyzed oxidation of 4-substituted 4-en-1-ol 40 and subsequent cyclization of the resulting anti-epoxy alcohol 41, and a similar oxidation-cyclization of 5-substituted 4-en-1-ol 49 by way of syn-epoxy alcohol 50. This was followed by construction of a third tetrahydrofuran ring by more conventional means. An improved synthesis of 1, which featured direct formation of bis(tetrahydrofuran) 51 from squalene derivative 66 by simultaneous double oxidation-cyclization, was also accomplished.

  DOI：

  10.1021/jo00007a013

文献信息

• Total synthesis of the meso-triterpene polyether teurilene
  作者：Masaru Hashimoto、Hiroko Harigaya、Mitsutoshi Yanagiya、Haruhisa Shirahama

  DOI：10.1021/jo00007a013

  日期：1991.3

  The first total synthesis of the triterpene ether teurilene (1) has been accomplished utilizing two vanadium(V)-catalyzed oxidation-cyclization reactions with different stereoselectivities. The synthesis involved stereoselective and step-by-step construction of 2,5-cis- and 2,5-trans-tetrahydrofuran rings, vanadium(V)-catalyzed oxidation of 4-substituted 4-en-1-ol 40 and subsequent cyclization of the resulting anti-epoxy alcohol 41, and a similar oxidation-cyclization of 5-substituted 4-en-1-ol 49 by way of syn-epoxy alcohol 50. This was followed by construction of a third tetrahydrofuran ring by more conventional means. An improved synthesis of 1, which featured direct formation of bis(tetrahydrofuran) 51 from squalene derivative 66 by simultaneous double oxidation-cyclization, was also accomplished.