ethyl 3-((2R,3aS,7R,7aR)-7-((tert-butyldimethylsilyl)oxy)-2-methoxy-3a-methyltetrahydro-2H-spiro[benzofuran-4,2'-[1,3]dioxolan]-7a(5H)-yl)propanoate | 935528-88-4

• 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 3-((2R,3aS,7R,7aR)-7-((tert-butyldimethylsilyl)oxy)-2-methoxy-3a-methyltetrahydro-2H-spiro[benzofuran-4,2'-[1,3]dioxolan]-7a(5H)-yl)propanoate
• CAS: 935528-88-4
• 化学式: C₂₃H₄₂O₇Si
• 分子量: 458.668
• InChiKey: VELOYCLRHAYEDZ-IVOMFYJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-((2R,3aS,7R,7aR)-7-((tert-butyldimethylsilyl)oxy)-2-methoxy-3a-methyltetrahydro-2H-spiro[benzofuran-4,2'-[1,3]dioxolan]-7a(5H)-yl)propanoate 在 palladium on activated charcoal 吡啶 、 邻苯二甲酸二甲酯 、 氢氟酸 、 potassium tert-butylate 、 氢气 、 四氯化钛 、 potassium carbonate 、 乙腈 、 calcium carbonate 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 42.33h， 生成 1-epi-pathylactone A
  参考文献：
  名称：

  Enantioselective Total Synthesis of 1-epi-Pathylactone A

  摘要：

  The first enantioselective total synthesis of 1-epi-pathylactone A, 3, has been accomplished using a PhI(OAc)(2)-mediated domino reaction as a key step. No diastereomeric separation was required throughout the whole synthetic scheme presented in this paper. Comparison of H-1 and C-13 NMR spectral data of the synthetic product with the reported spectral data of natural pathylactone A, coupled with an X-ray crystallographic analysis, led to the conclusion that the C1 configuration in the original paper was erroneously ascribed to (R).

  DOI：

  10.1021/ol070207y
• 作为产物：
  描述：

  ethyl (E)-3-((2R,3aS,7R,7aR)-7-((tert-butyldimethylsilyl)oxy)-2-methoxy-3a-methyltetrahydro-2H-spiro[benzofuran-4,2'-[1,3]dioxolan]-7a(5H)-yl)acrylate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以77%的产率得到ethyl 3-((2R,3aS,7R,7aR)-7-((tert-butyldimethylsilyl)oxy)-2-methoxy-3a-methyltetrahydro-2H-spiro[benzofuran-4,2'-[1,3]dioxolan]-7a(5H)-yl)propanoate
  参考文献：
  名称：

  Enantioselective Total Synthesis of 1-epi-Pathylactone A

  摘要：

  The first enantioselective total synthesis of 1-epi-pathylactone A, 3, has been accomplished using a PhI(OAc)(2)-mediated domino reaction as a key step. No diastereomeric separation was required throughout the whole synthetic scheme presented in this paper. Comparison of H-1 and C-13 NMR spectral data of the synthetic product with the reported spectral data of natural pathylactone A, coupled with an X-ray crystallographic analysis, led to the conclusion that the C1 configuration in the original paper was erroneously ascribed to (R).

  DOI：

  10.1021/ol070207y