(1R,3S,4S,6R)-7-Oxa-bicyclo[4.1.0]heptane-3,4-dicarboxylic acid di-tert-butyl ester | 371974-94-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1R,3S,4S,6R)-7-Oxa-bicyclo[4.1.0]heptane-3,4-dicarboxylic acid di-tert-butyl ester
• 英文别名: ditert-butyl (1R,3S,4S,6R)-7-oxabicyclo[4.1.0]heptane-3,4-dicarboxylate
• CAS: 371974-94-6
• 化学式: C₁₆H₂₆O₅
• 分子量: 298.379
• InChiKey: NCBIWVAAAWSMLG-NNYUYHANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,3S,4S,6R)-7-Oxa-bicyclo[4.1.0]heptane-3,4-dicarboxylic acid di-tert-butyl ester 在 cerium(IV) triflate 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以89%的产率得到(1S,2S,4S,5S)-4,5-Dihydroxy-cyclohexane-1,2-dicarboxylic acid
  参考文献：
  名称：

  Stereoselective Synthesis of Conformationally Constrained Cyclohexanediols:  A Set of Molecular Scaffolds for the Synthesis of Glycomimetics

  摘要：

  The practical, stereoselective synthesis of the three diastereoisomeric 1,2-trans-dicarboxy-4,5-cyclohexanediols. 1-3 (DCCHDs) is described, starting from a common precursor, easily available in both enantiomeric forms. The regioselective derivatization of all functional groups of I is also reported. The three DCCHDs are locked in a single chair conformation and thus can be used to mimic vicinally disubstituted monosaccharides of any relative configuration.

  DOI：

  10.1021/jo015570b
• 作为产物：
  描述：

  N,N-二甲基甲酰胺二叔丁基缩醛 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 39.0h， 生成 (1R,3S,4S,6R)-7-Oxa-bicyclo[4.1.0]heptane-3,4-dicarboxylic acid di-tert-butyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Conformationally Constrained Cyclohexanediols:  A Set of Molecular Scaffolds for the Synthesis of Glycomimetics

  摘要：

  The practical, stereoselective synthesis of the three diastereoisomeric 1,2-trans-dicarboxy-4,5-cyclohexanediols. 1-3 (DCCHDs) is described, starting from a common precursor, easily available in both enantiomeric forms. The regioselective derivatization of all functional groups of I is also reported. The three DCCHDs are locked in a single chair conformation and thus can be used to mimic vicinally disubstituted monosaccharides of any relative configuration.

  DOI：

  10.1021/jo015570b