(2R,3R,3aS,6aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-tetrahydro-3a-hydroxy-6a-(hydroxymethyl)furo[3,4-b]furan-6-(6aH)-one | 1429481-05-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,3aS,6aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-tetrahydro-3a-hydroxy-6a-(hydroxymethyl)furo[3,4-b]furan-6-(6aH)-one
• 英文别名: (2R,3R,3aS,6aS)-3a-hydroxy-6a-(hydroxymethyl)-3-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-furo[3,4-b]furan-6-one
• CAS: 1429481-05-9
• 化学式: C₂₂H₂₄O₇
• 分子量: 400.428
• InChiKey: BAEKNEXHDHDKKL-KRXUUXHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  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 tert-butyl (4aS,6R,7R,7aS)-7-(benzyloxy)-4a-dodecyltetrahydro-6-(hydroxymethyl)-2,2-dimethyl-4H-furo[3,2-d][1,3]-dioxine-7a-carboxylate
  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
• 作为产物：
  描述：

  在 草酰氯 、 N,N-二甲基甲酰胺 、 甲醇 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 5.0h， 以1.7g的产率得到(2R,3R,3aS,6aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-tetrahydro-3a-hydroxy-6a-(hydroxymethyl)furo[3,4-b]furan-6-(6aH)-one
  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.