methyl 2-((3aR,4aS,5aR,7S,8R,9aS,10aR,12aS)-8,9a-dimethyl-2-oxo-8-((trimethylsilyl)oxy)tetradecahydrofuro[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin-7-yl)acetate | 1095601-74-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-((3aR,4aS,5aR,7S,8R,9aS,10aR,12aS)-8,9a-dimethyl-2-oxo-8-((trimethylsilyl)oxy)tetradecahydrofuro[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin-7-yl)acetate
• CAS: 1095601-74-3
• 化学式: C₂₂H₃₆O₈Si
• 分子量: 456.609
• InChiKey: PDAIVQHGMZXGPC-WUKXMCLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 2-((3aR,4aS,5aR,7S,8R,9aS,10aR,12aS)-8,9a-dimethyl-2-oxo-8-((trimethylsilyl)oxy)tetradecahydrofuro[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin-7-yl)acetate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 C₂₁H₃₆O₇Si
  参考文献：
  名称：

  Stereoselective Synthesis of trans-Fused 7,6,6,7-Membered Tetracyclic Ether, Corresponding to the EFGH-Ring of Gambierol and the BCDE-Ring of Gambieric Acids

  摘要：

  Stereoselective synthesis of a trans-fused 7,6,6,7-membered tetracyclic ether, corresponding to the EFGH-ring of gambierol and the BCDE-ring of gambieric acids, was efficiently accomplished via a two-directional approach. The key reactions were SMI2-induced double cyclization for construction of the F- and H-rings and SMI2-induced cyclization followed by ring expansion for construction of the E-ring.

  DOI：

  10.1021/ol8024555
• 作为产物：
  描述：

  三氟甲磺酸三甲基硅酯 、 methyl 2-[(1S,3R,7S,10R,12S,14R,15S,17R)-14-hydroxy-12,14-dimethyl-5-oxo-2,6,11,16-tetraoxatetracyclo[8.8.0.03,7.012,17]octadecan-15-yl]acetate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到methyl 2-((3aR,4aS,5aR,7S,8R,9aS,10aR,12aS)-8,9a-dimethyl-2-oxo-8-((trimethylsilyl)oxy)tetradecahydrofuro[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin-7-yl)acetate
  参考文献：
  名称：

  Stereoselective Synthesis of trans-Fused 7,6,6,7-Membered Tetracyclic Ether, Corresponding to the EFGH-Ring of Gambierol and the BCDE-Ring of Gambieric Acids

  摘要：

  Stereoselective synthesis of a trans-fused 7,6,6,7-membered tetracyclic ether, corresponding to the EFGH-ring of gambierol and the BCDE-ring of gambieric acids, was efficiently accomplished via a two-directional approach. The key reactions were SMI2-induced double cyclization for construction of the F- and H-rings and SMI2-induced cyclization followed by ring expansion for construction of the E-ring.

  DOI：

  10.1021/ol8024555