((4aS,6R,7R,7aS)-7-(benzyloxy)-6-((benzyloxy)methyl)-4a-(dodec-1-enyl)tetrahydro-2,2-dimethyl-4H-furo[3,2-d][1,3]-dioxin-7a-yl)methanol | 1429481-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((4aS,6R,7R,7aS)-7-(benzyloxy)-6-((benzyloxy)methyl)-4a-(dodec-1-enyl)tetrahydro-2,2-dimethyl-4H-furo[3,2-d][1,3]-dioxin-7a-yl)methanol
• 英文别名: [(4aS,6R,7R,7aS)-4a-[(E)-dodec-1-enyl]-2,2-dimethyl-7-phenylmethoxy-6-(phenylmethoxymethyl)-6,7-dihydro-4H-furo[3,2-d][1,3]dioxin-7a-yl]methanol
• CAS: 1429481-10-6
• 化学式: C₃₆H₅₂O₆
• 分子量: 580.805
• InChiKey: WZDNZDXIZLVHMK-XQZLAWLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2R,3R,3aS,6aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-tetrahydro-3a-hydroxy-6a-(hydroxymethyl)furo[3,4-b]furan-6-(6aH)-one 在 正丁基锂 、 水 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 正己烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 21.5h， 生成 ((4aS,6R,7R,7aS)-7-(benzyloxy)-6-((benzyloxy)methyl)-4a-(dodec-1-enyl)tetrahydro-2,2-dimethyl-4H-furo[3,2-d][1,3]-dioxin-7a-yl)methanol 、 ((4aS,6R,7R,7aS)-7-(benzyloxy)-6-((benzyloxy)methyl)-4a-(dodec-1-enyl)tetrahydro-2,2-dimethyl-4H-furo[3,2-d][1,3]-dioxin-7a-yl)methanol
  参考文献：
  名称：

  Total Synthesis of (−)-Cinatrin C₁ Based on an In(OTf)₃-Catalyzed Conia-Ene Reaction

  摘要：

  The stereocontrolled total synthesis of (-)-cinatrin C-1, a phospholipase A(2) inhibitor, has been accomplished. The key feature includes the stereoselective construction of the highly substituted tetrahydrofuran core by In(OTf)(3)-catalyzed Conia-ene reaction of the oxygen-tethered acetylenic malonic ester followed by dihydroxylation with concomitant lactonization.

  DOI：

  10.1021/jo400263w

文献信息

• Total Synthesis of (−)-Cinatrin C₁ Based on an In(OTf)₃-Catalyzed Conia-Ene Reaction
  作者：Fumiya Urabe、Shunsuke Nagashima、Keisuke Takahashi、Jun Ishihara、Susumi Hatakeyama

  DOI：10.1021/jo400263w

  日期：2013.4.19

  The stereocontrolled total synthesis of (-)-cinatrin C-1, a phospholipase A(2) inhibitor, has been accomplished. The key feature includes the stereoselective construction of the highly substituted tetrahydrofuran core by In(OTf)(3)-catalyzed Conia-ene reaction of the oxygen-tethered acetylenic malonic ester followed by dihydroxylation with concomitant lactonization.