ethyl (E)-2-methyl-4-[(2R,4S)-5-oxo-2-phenyl-1,3-dioxan-4-yl]but-2-enoate | 131310-95-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-2-methyl-4-[(2R,4S)-5-oxo-2-phenyl-1,3-dioxan-4-yl]but-2-enoate
• CAS: 131310-95-7
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: HNDRFVLAIVWWNE-FMUPAYBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-methyl-4-[(2R,4S)-5-oxo-2-phenyl-1,3-dioxan-4-yl]but-2-enoate 在 Oxone 、 sodium hypochlorite 、 Shi's ketone 、 2,2,6,6-四甲基哌啶氧化物 、 potassium tert-butylate 、 碳酸氢钠 、 potassium bromide 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.78h， 生成 (2R,4S,5R)-4-[[(2R,3R)-3-ethenyl-3-methyloxiran-2-yl]methyl]-5-methyl-2-phenyl-1,3-dioxan-5-ol
  参考文献：
  名称：

  A Facile and Practical Synthesis of Nicolaou's Key Intermediates, 2-Methyl- and 2,6-Dimethyltetrahydropyrans, toward the Total Synthesis of Ladder-Shaped Polyethers

  摘要：

  A facile and robust method to prepare 2-methyl-and 2,6-dimethyltetrahydropyrans, most useful Nicolaou intermediates for the synthesis of ladder-shaped polyethers, is disclosed. The established highly practical recipe, adopting chemo-and stereoselective catalytic oxidations and one-pot reactions with few chromatographic purifications, would significantly facilitate the large-scale supply of pivotal monocyclic building blocks, which is a rate-determining process of gigantic tetrahydropyran-containing natural products synthesis.

  DOI：

  10.1055/s-0033-1338503
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 sodium hypochlorite 、 2-氮杂金刚烷-N-氧自由基 、 D(+)-10-樟脑磺酸 、 碳酸氢钠 、 potassium bromide 、 原甲酸三甲酯 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成 ethyl (E)-2-methyl-4-[(2R,4S)-5-oxo-2-phenyl-1,3-dioxan-4-yl]but-2-enoate
  参考文献：
  名称：

  A Facile and Practical Synthesis of Nicolaou's Key Intermediates, 2-Methyl- and 2,6-Dimethyltetrahydropyrans, toward the Total Synthesis of Ladder-Shaped Polyethers

  摘要：

  A facile and robust method to prepare 2-methyl-and 2,6-dimethyltetrahydropyrans, most useful Nicolaou intermediates for the synthesis of ladder-shaped polyethers, is disclosed. The established highly practical recipe, adopting chemo-and stereoselective catalytic oxidations and one-pot reactions with few chromatographic purifications, would significantly facilitate the large-scale supply of pivotal monocyclic building blocks, which is a rate-determining process of gigantic tetrahydropyran-containing natural products synthesis.

  DOI：

  10.1055/s-0033-1338503

文献信息

• A Facile and Practical Synthesis of Nicolaou's Key Intermediates, 2-Methyl- and 2,6-Dimethyltetrahydropyrans, toward the Total Synthesis of Ladder-Shaped Polyethers
  作者：Kohei Torikai、Takeharu Nakashima、Tomomi Baba、Hisaaki Onoue、Wataru Yamashita

  DOI：10.1055/s-0033-1338503

  日期：——

  A facile and robust method to prepare 2-methyl-and 2,6-dimethyltetrahydropyrans, most useful Nicolaou intermediates for the synthesis of ladder-shaped polyethers, is disclosed. The established highly practical recipe, adopting chemo-and stereoselective catalytic oxidations and one-pot reactions with few chromatographic purifications, would significantly facilitate the large-scale supply of pivotal monocyclic building blocks, which is a rate-determining process of gigantic tetrahydropyran-containing natural products synthesis.