(1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-5-oxocyclohexane-1,2-dicarboxylic acid di-tert-butyl ester | 371975-08-5

• 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-(tert-butyldimethylsilyloxy)-5-oxocyclohexane-1,2-dicarboxylic acid di-tert-butyl ester
• 英文别名: ditert-butyl (1S,2S,4R)-4-[tert-butyl(dimethyl)silyl]oxy-5-oxocyclohexane-1,2-dicarboxylate
• CAS: 371975-08-5
• 化学式: C₂₂H₄₀O₆Si
• 分子量: 428.641
• InChiKey: YNXWXVDOKSPIQJ-YQQAZPJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-5-oxocyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (1S,2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 、 (1S,2S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-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：

  N,N-二甲基甲酰胺二叔丁基缩醛 在 咪唑 、 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 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 64.5h， 生成 (1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-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

文献信息

• Stereoselective Synthesis of Conformationally Constrained Cyclohexanediols:  A Set of Molecular Scaffolds for the Synthesis of Glycomimetics
  作者：Anna Bernardi、Daniela Arosio、Leonardo Manzoni、Fabrizio Micheli、Alessandra Pasquarello、Pierfausto Seneci

  DOI：10.1021/jo015570b

  日期：2001.9.1

  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.