dimethyl 2-((2R,3S)-1,3-bis(benzyloxy)pent-4-yn-2-yloxy)-malonate | 1429481-00-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 2-((2R,3S)-1,3-bis(benzyloxy)pent-4-yn-2-yloxy)-malonate
• 英文别名: dimethyl 2-[(2R,3S)-1,3-bis(phenylmethoxy)pent-4-yn-2-yl]oxypropanedioate
• CAS: 1429481-00-4
• 化学式: C₂₄H₂₆O₇
• 分子量: 426.466
• InChiKey: LGIQTEFXTUIXGF-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 2-((2R,3S)-1,3-bis(benzyloxy)pent-4-yn-2-yloxy)-malonate 在 indium(III) triflate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以96%的产率得到dimethyl (4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-dihydro-3-methylene-furan-2,2-(3H)-dicarboxylate
  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：

  (2R,3R)-3-hydroxy-2,3-bis(benzylyloxy)propionaldehyde 在 甲醇 、 dirhodium tetraacetate 、 potassium carbonate 作用下， 以 苯 为溶剂， 反应 10.0h， 生成 dimethyl 2-((2R,3S)-1,3-bis(benzyloxy)pent-4-yn-2-yloxy)-malonate
  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.