(2R,3R,5R)-5-[(1S,3E)-1-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-3-hexen-1-yl]tetrahydro-2-[(2E)-5-(trimethylsilyl)-2-penten-4-yn-1-yl]-3-furanol | 199175-12-7

• 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-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-3-hexen-1-yl]tetrahydro-2-[(2E)-5-(trimethylsilyl)-2-penten-4-yn-1-yl]-3-furanol
• 英文别名: (2R,3R,5R)-5-[(E,1S)-1-[tert-butyl(dimethyl)silyl]oxyhex-3-enyl]-2-[(E)-5-trimethylsilylpent-2-en-4-ynyl]oxolan-3-ol
• CAS: 199175-12-7
• 化学式: C₂₄H₄₄O₃Si₂
• 分子量: 436.783
• InChiKey: NLWUIIKMDBIYNU-ICIGPFSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.08
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R,5R)-5-[(1S,3E)-1-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-3-hexen-1-yl]tetrahydro-2-[(2E)-5-(trimethylsilyl)-2-penten-4-yn-1-yl]-3-furanol 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以89 mg的产率得到(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
• 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 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.25h， 生成 (2R,3R,5R)-5-[(1S,3E)-1-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-3-hexen-1-yl]tetrahydro-2-[(2E)-5-(trimethylsilyl)-2-penten-4-yn-1-yl]-3-furanol
  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

• Radical cyclization of β-alkoxyacrylates: Stereoselective synthesis of (−)-trans-Kumausyne
  作者：Eun Lee、Sang-Ku Yoo、Young-Shin Cho、Hwan-Sung Cheon、You Hoon Chong

  DOI：10.1016/s0040-4039(97)10070-3

  日期：1997.11

  (−)-trans-Kumausyne was synthesized from D-(+)-xylose. Radical cyclization reaction of a β-alkoxyacrylate intermediate proceeded stereoselectively to give a tetrahydrofuranyl product with correct stereochemistry.

  （-）-反式-Kumausyne是由D-（+）-木糖合成的。β-烷氧基丙烯酸酯中间体的自由基环化反应进行立体选择，得到具有正确立体化学的四氢呋喃基产物。
• 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.