methyl (2R,3R,3aS,6aR)-3-(benzyloxy)-2-((benzyloxy)-methyl)-3a-hydroxy-6-oxohexahydrofuro[3,4-b]furan-6a-carboxylate | 1429481-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2R,3R,3aS,6aR)-3-(benzyloxy)-2-((benzyloxy)-methyl)-3a-hydroxy-6-oxohexahydrofuro[3,4-b]furan-6a-carboxylate
• 英文别名: methyl (2R,3R,3aS,6aR)-3a-hydroxy-6-oxo-3-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-furo[3,4-b]furan-6a-carboxylate
• CAS: 1429481-02-6
• 化学式: C₂₃H₂₄O₈
• 分子量: 428.439
• InChiKey: ZJBGOKUQMLUFBM-PJIZGREPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2R,3R)-3-hydroxy-2,3-bis(benzylyloxy)propionaldehyde 在 indium(III) triflate 、 甲醇 、 dirhodium tetraacetate 、 四氧化锇 、 potassium carbonate 、 N-甲基吗啉氧化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 苯硼酸 作用下， 以 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 44.0h， 生成 methyl (2R,3R,3aS,6aR)-3-(benzyloxy)-2-((benzyloxy)-methyl)-3a-hydroxy-6-oxohexahydrofuro[3,4-b]furan-6a-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

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.