ethyl (E,4S)-4-[(2S,3R)-3-(hydroxymethyl)oxiran-2-yl]-4-(methoxymethoxy)but-2-enoate | 1141379-68-1

• 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,4S)-4-[(2S,3R)-3-(hydroxymethyl)oxiran-2-yl]-4-(methoxymethoxy)but-2-enoate
• CAS: 1141379-68-1
• 化学式: C₁₁H₁₈O₆
• 分子量: 246.26
• InChiKey: NGSVUDGAYBNNJL-ORARJGFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (E,4S)-4-[(2S,3R)-3-(hydroxymethyl)oxiran-2-yl]-4-(methoxymethoxy)but-2-enoate 在 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 ethyl 2-[(1R,4S,5S,6R)-5-(methoxymethoxy)-3,7-dioxabicyclo[4.1.0]heptan-4-yl]acetate 、
  参考文献：
  名称：

  Diastereoselective construction of substituted tetrahydropyrans using an intramolecular oxy-Michael strategy

  摘要：

  The highly diastereoselective construction of Substituted tetrahydropyrans, a common core segment (C3-C10) of the thiomarinols and the pseudomonic acid antibiotics, has been accomplished using the intramolecular oxy-Michael reaction under both basic and high-pressure conditions followed by regio- and stereoselective epoxide opening with acetylide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.084
• 作为产物：
  描述：

  C₂₅H₃₂O₅Si 、 氯甲基甲基醚 在 N,N-二异丙基乙胺 、 四丁基氟化铵 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 以66%的产率得到ethyl (E,4S)-4-[(2S,3R)-3-(hydroxymethyl)oxiran-2-yl]-4-(methoxymethoxy)but-2-enoate
  参考文献：
  名称：

  Diastereoselective construction of substituted tetrahydropyrans using an intramolecular oxy-Michael strategy

  摘要：

  The highly diastereoselective construction of Substituted tetrahydropyrans, a common core segment (C3-C10) of the thiomarinols and the pseudomonic acid antibiotics, has been accomplished using the intramolecular oxy-Michael reaction under both basic and high-pressure conditions followed by regio- and stereoselective epoxide opening with acetylide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.084

文献信息

• Diastereoselective construction of substituted tetrahydropyrans using an intramolecular oxy-Michael strategy
  作者：Fumika Yakushiji、Jacques Maddaluno、Masahiro Yoshida、Kozo Shishido

  DOI：10.1016/j.tetlet.2009.01.084

  日期：2009.4

  The highly diastereoselective construction of Substituted tetrahydropyrans, a common core segment (C3-C10) of the thiomarinols and the pseudomonic acid antibiotics, has been accomplished using the intramolecular oxy-Michael reaction under both basic and high-pressure conditions followed by regio- and stereoselective epoxide opening with acetylide. (C) 2009 Elsevier Ltd. All rights reserved.