(1S,2S,4R)-4-Hydroxy-5-oxo-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester | 371975-04-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (1S,2S,4R)-4-Hydroxy-5-oxo-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester
• 英文别名: ditert-butyl (1S,2S,4R)-4-hydroxy-5-oxocyclohexane-1,2-dicarboxylate
• CAS: 371975-04-1
• 化学式: C₁₆H₂₆O₆
• 分子量: 314.379
• InChiKey: PDSUOKPZHNGRHB-GARJFASQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (1S,2S,4R)-4-Hydroxy-5-oxo-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到(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
• 作为产物：
  描述：

  (1S,2S)-cyclohex-4-ene-1,2-dicarboxylic acid di-tert-butyl ester 在 osmium (III) chloride 、 N,N-二乙基乙胺氧化物 、 水 、 二正丁基氧化锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 13.5h， 生成 (1S,2S,4R)-4-Hydroxy-5-oxo-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