(1S,2S,4R)-4-acetoxy-5-oxocyclohexane-1,2-dicarboxylic acid di-tert-butyl ester | 371975-10-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2S,4R)-4-acetoxy-5-oxocyclohexane-1,2-dicarboxylic acid di-tert-butyl ester
• 英文别名: ditert-butyl (1S,2S,4R)-4-acetyloxy-5-oxocyclohexane-1,2-dicarboxylate
• CAS: 371975-10-9
• 化学式: C₁₈H₂₈O₇
• 分子量: 356.416
• InChiKey: OTNBIXIVOSTXAX-SGMGOOAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R)-4-acetoxy-5-oxocyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (1S,2S,4R,5S)-4-Acetoxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 、 (1S,2S,4R,5R)-4-Acetoxy-5-hydroxy-cyclohexane-1,2-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
• 作为产物：
  描述：

  ditert-butyl (1S,2S,4S,5R)-4,5-dihydroxycyclohexane-1,2-dicarboxylate 在 吡啶 、 4-二甲氨基吡啶 、 二正丁基氧化锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 14.5h， 生成 (1S,2S,4R)-4-acetoxy-5-oxocyclohexane-1,2-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