ethyl (E)-3-[(7R,9R)-9-[(E)-3-ethoxy-3-oxoprop-1-enyl]-6,10-dioxaspiro[4.5]decan-7-yl]prop-2-enoate | 474005-86-2

• 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)-3-[(7R,9R)-9-[(E)-3-ethoxy-3-oxoprop-1-enyl]-6,10-dioxaspiro[4.5]decan-7-yl]prop-2-enoate
• CAS: 474005-86-2
• 化学式: C₁₈H₂₆O₆
• 分子量: 338.401
• InChiKey: GONLZRPYLKXTTJ-KRJFFLAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-[(7R,9R)-9-[(E)-3-ethoxy-3-oxoprop-1-enyl]-6,10-dioxaspiro[4.5]decan-7-yl]prop-2-enoate 在 吡啶 、 4-二甲氨基吡啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 (R,R)-DPPBA 、 camphor-10-sulfonic acid 、 水 、 二异丁基氢化铝 、 溶剂黄146 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 Acetic acid (E)-3-[(2R,4R,5S)-5-(2-hydroxy-ethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-allyl ester
  参考文献：
  名称：

  A Novel Route to the F-Ring of Halichondrin B. Diastereoselection in Pd(0)-Mediated meso and C₂ Diol Desymmetrization

  摘要：

  [GRAPHICS]Both sigma and C-2 symmetric diol diacetates were synthesized via two-directional chain elongation. A palladium-mediated, ligand-controlled C-2 diol desymmetrization provided the desired tetrahydrofuran with the correct relative and absolute stereochemistries. Simple functional group manipulation led to the desired F-ring of halichondrin B. Desymmetrization of the meso substrate enantioselectively provided the diastereomer, leading to a refinement of our understanding of the transition state model.

  DOI：

  10.1021/ol026504e
• 作为产物：
  描述：

  (3R,5R)-hepta-1,6-diene-3,5-diol 在 4-甲基苯磺酸吡啶 、 臭氧 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 8.0h， 生成 ethyl (E)-3-[(7R,9R)-9-[(E)-3-ethoxy-3-oxoprop-1-enyl]-6,10-dioxaspiro[4.5]decan-7-yl]prop-2-enoate
  参考文献：
  名称：

  A Novel Route to the F-Ring of Halichondrin B. Diastereoselection in Pd(0)-Mediated meso and C₂ Diol Desymmetrization

  摘要：

  [GRAPHICS]Both sigma and C-2 symmetric diol diacetates were synthesized via two-directional chain elongation. A palladium-mediated, ligand-controlled C-2 diol desymmetrization provided the desired tetrahydrofuran with the correct relative and absolute stereochemistries. Simple functional group manipulation led to the desired F-ring of halichondrin B. Desymmetrization of the meso substrate enantioselectively provided the diastereomer, leading to a refinement of our understanding of the transition state model.

  DOI：

  10.1021/ol026504e

文献信息

• A Novel Route to the F-Ring of Halichondrin B. Diastereoselection in Pd(0)-Mediated <i>meso</i> and <i>C</i>₂ Diol Desymmetrization
  作者：Lei Jiang、Steven D. Burke

  DOI：10.1021/ol026504e

  日期：2002.10.1

  [GRAPHICS]Both sigma and C-2 symmetric diol diacetates were synthesized via two-directional chain elongation. A palladium-mediated, ligand-controlled C-2 diol desymmetrization provided the desired tetrahydrofuran with the correct relative and absolute stereochemistries. Simple functional group manipulation led to the desired F-ring of halichondrin B. Desymmetrization of the meso substrate enantioselectively provided the diastereomer, leading to a refinement of our understanding of the transition state model.