(E,2S,3S)-2-methyl-5-phenyl-3-trimethylsilyloxypent-4-enal | 913066-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E,2S,3S)-2-methyl-5-phenyl-3-trimethylsilyloxypent-4-enal
• CAS: 913066-83-8
• 化学式: C₁₅H₂₂O₂Si
• 分子量: 262.424
• InChiKey: ACHLUXVOPJTVCO-NFGUQPCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E,2S,3S)-2-methyl-5-phenyl-3-trimethylsilyloxypent-4-enal 在 titanium(IV) isopropylate 、 盐酸 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 ruthenium carbene complex 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 (+)-Weinsaeure-diethylester 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 63.0h， 生成 Toluene-4-sulfonic acid (S)-2-hydroxy-2-[(2R,4R,5R,6S)-4-hydroxy-5-methyl-6-((E)-styryl)-tetrahydro-pyran-2-yl]-ethyl ester
  参考文献：
  名称：

  Synthesis of the C29−C37 Bicyclic Ether Core of (+)-Sorangicin A

  摘要：

  Construction of the unique bicyclic bis-ether core of the macrolide (+)-sorangicin A has been achieved. This fragment was prepared by utilizing a one-pot cascade of three bond forming events. An epoxide opening of the epoxy tosylate 2 led to the formation of the tetrahydropyran and subsequently to a second epoxide. Finally, a second epoxide opening closed the tetrahydrofuran ring. The bicyclic fragment was synthesized in just nine steps from (E)-cinnamaldehyde.

  DOI：

  10.1021/ol061339e
• 作为产物：
  描述：

  (E)-(2S,3S)-1-((S)-4-Benzyl-2-thioxo-thiazolidin-3-yl)-2-methyl-5-phenyl-3-trimethylsilanyloxy-pent-4-en-1-one 在 二异丁基氢化铝 、 Rochelle's salt 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以76%的产率得到(E,2S,3S)-2-methyl-5-phenyl-3-trimethylsilyloxypent-4-enal
  参考文献：
  名称：

  Synthesis of the C29−C37 Bicyclic Ether Core of (+)-Sorangicin A

  摘要：

  Construction of the unique bicyclic bis-ether core of the macrolide (+)-sorangicin A has been achieved. This fragment was prepared by utilizing a one-pot cascade of three bond forming events. An epoxide opening of the epoxy tosylate 2 led to the formation of the tetrahydropyran and subsequently to a second epoxide. Finally, a second epoxide opening closed the tetrahydrofuran ring. The bicyclic fragment was synthesized in just nine steps from (E)-cinnamaldehyde.

  DOI：

  10.1021/ol061339e

文献信息

• Synthesis of the C29−C37 Bicyclic Ether Core of (+)-Sorangicin A
  作者：Michael T. Crimmins、Matthew W. Haley

  DOI：10.1021/ol061339e

  日期：2006.9

  Construction of the unique bicyclic bis-ether core of the macrolide (+)-sorangicin A has been achieved. This fragment was prepared by utilizing a one-pot cascade of three bond forming events. An epoxide opening of the epoxy tosylate 2 led to the formation of the tetrahydropyran and subsequently to a second epoxide. Finally, a second epoxide opening closed the tetrahydrofuran ring. The bicyclic fragment was synthesized in just nine steps from (E)-cinnamaldehyde.