(2S,3R,4R,6R)-3-Methyl-6-(S)-oxiranyl-2-((E)-styryl)-tetrahydro-pyran-4-ol | 913066-80-5

• 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: (2S,3R,4R,6R)-3-Methyl-6-(S)-oxiranyl-2-((E)-styryl)-tetrahydro-pyran-4-ol
• 英文别名: (2S,3R,4R,6R)-3-methyl-6-[(2S)-oxiran-2-yl]-2-[(E)-2-phenylethenyl]oxan-4-ol
• CAS: 913066-80-5
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: WLSAIJAGQOCWSB-BVTIQWBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,6R)-3-Methyl-6-(S)-oxiranyl-2-((E)-styryl)-tetrahydro-pyran-4-ol 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 [(1R,3S,4R,5R,7R)-4-methyl-3-[(E)-2-phenylethenyl]-2,6-dioxabicyclo[3.2.1]octan-7-yl]methanol
  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：

  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 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (2S,3R,4R,6R)-3-Methyl-6-(S)-oxiranyl-2-((E)-styryl)-tetrahydro-pyran-4-ol
  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