(1S,2R,3S,4R)-7-Oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid mono-((R)-benzyloxycarbonyl-phenyl-methyl) ester | 131564-21-1

• 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: (1S,2R,3S,4R)-7-Oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid mono-((R)-benzyloxycarbonyl-phenyl-methyl) ester
• 英文别名: (1R,2S,3R,4S)-3-[(1R)-2-oxo-1-phenyl-2-phenylmethoxyethoxy]carbonyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid
• CAS: 131564-21-1
• 化学式: C₂₃H₂₂O₇
• 分子量: 410.423
• InChiKey: LCTJBHPVVMVEHB-UJMXGEILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  扁桃酸苯酯 、 cis-5-norbornene-endo-2,3-dicarboxylic anhydride 在 正丁基锂 作用下， 生成 (1R,2S,3R,4S)-7-Oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid mono-((R)-benzyloxycarbonyl-phenyl-methyl) ester 、 (1S,2R,3S,4R)-7-Oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid mono-((R)-benzyloxycarbonyl-phenyl-methyl) ester
  参考文献：
  名称：

  Highly effective and practical enantioselective synthesis of half-esters of bicyclo[2.2.1]heptanedicarboxylic acid

  摘要：

  An effective and practical enantioselective synthesis of half-esters of bicyclo[2.2.1]heptane-2,3-dicarboxylic acid was developed by enantioselective fission of sigma-symmetrical cyclic anhydrides with chiral mandelic acid derivatives, followed by deprotection of the mandelate moiety, crystallization, and further modification. These half-esters are very attractive chiral building blocks for numerous natural products, and this new method makes possible their synthesis via common intermediates with high optical purity.

  DOI：

  10.1021/jo00013a009