(2R,3R,5R)-5-[(1S,3E)-1-TBS-hydroxyhex-3-en-1-yl]-2-[(2E)-pent-2-en-4-yn-1-yl]tetrahydrofuran-3-ol | 1312930-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,5R)-5-[(1S,3E)-1-TBS-hydroxyhex-3-en-1-yl]-2-[(2E)-pent-2-en-4-yn-1-yl]tetrahydrofuran-3-ol
• 英文别名: (2R,3R,5R)-5-[(E,1S)-1-[tert-butyl(dimethyl)silyl]oxyhex-3-enyl]-2-[(E)-pent-2-en-4-ynyl]oxolan-3-ol
• CAS: 1312930-32-7
• 化学式: C₂₁H₃₆O₃Si
• 分子量: 364.601
• InChiKey: HLBGKUOLZVWTCL-GFOJEKOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3aR,5R,6aR)-5-[(1S)-1-hydroxybut-3-en-1-yl]tetrahydrofuro[3,2-b]furan-2(3H)-one 在 咪唑 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 正丁基锂 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.25h， 生成 (2R,3R,5R)-5-[(1S,3E)-1-TBS-hydroxyhex-3-en-1-yl]-2-[(2E)-pent-2-en-4-yn-1-yl]tetrahydrofuran-3-ol
  参考文献：
  名称：

  Stereoselective Total Synthesis of (−)-Kumausallene

  摘要：

  A stereoselective total synthesis of (-)-kumausallene was completed in 12 steps from acetylacetone. The hidden symmetry of (-)-kumausallene was recognized, and its skeleton was constructed efficiently from a C(2)-symmetric diol by a palladium-catalyzed cascade reaction. High diastereoselectivity was observed for the DMF-promoted biomimetic 1,4-bromocyclization of a conjugated enyne.

  DOI：

  10.1021/ol201477u

文献信息

• Stereoselective Total Synthesis of (−)-Kumausallene
  作者：Jenny B. Werness、Weiping Tang

  DOI：10.1021/ol201477u

  日期：2011.7.15

  A stereoselective total synthesis of (-)-kumausallene was completed in 12 steps from acetylacetone. The hidden symmetry of (-)-kumausallene was recognized, and its skeleton was constructed efficiently from a C(2)-symmetric diol by a palladium-catalyzed cascade reaction. High diastereoselectivity was observed for the DMF-promoted biomimetic 1,4-bromocyclization of a conjugated enyne.