(R)-3-((4S,5S)-4-Cyclohexylmethyl-2-oxo-oxazolidin-5-yl)-2-methyl-propionic acid | 147426-18-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-((4S,5S)-4-Cyclohexylmethyl-2-oxo-oxazolidin-5-yl)-2-methyl-propionic acid
• 英文别名: (2R)-3-[(4S,5S)-4-(cyclohexylmethyl)-2-oxo-1,3-oxazolidin-5-yl]-2-methylpropanoic acid
• CAS: 147426-18-4
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: DRXDTZFRHPSKLS-USWWRNFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-((4S,5S)-4-Cyclohexylmethyl-2-oxo-oxazolidin-5-yl)-2-methyl-propionic acid 在 红铝 作用下， 生成 (4S,5S)-4-Cyclohexylmethyl-5-((R)-3-hydroxy-2-methyl-propyl)-oxazolidin-2-one
  参考文献：
  名称：

  A short stereocontrolled synthesis of hydroxyethylene dipeptide isosteres

  摘要：

  A stereocontrolled synthesis of protected hydroxyethylene dipeptide isosteres 14 and 16 is described. It provides the 2R,4S,5S epimers required for the preparation of aspartic proteinase inhibitors. The choice of a benzene ring as a precursor to the carboxylic acid function has enabled us to use the readily accessible chiral Grignard reagent 3 which reacts with the protected alpha-amino aldehyde 8 stereoselectively. Kilogram quantities of 16 have been produced by this route in a satisfactory overall yield. The combination of N- and 0-protecting groups employed facilitates the incorporation of 14 or 16 into peptide-based enzyme inhibitors.

  DOI：

  10.1021/jo00060a052
• 作为产物：
  描述：

  (2R,4S,5S)-5-<(tert-butyloxycarbonyl)amino>-6-cyclohexyl-4-hydroxy-2-phenylhexane 在 sodium periodate 、 四氧化钌 、 sodium hydride 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (R)-3-((4S,5S)-4-Cyclohexylmethyl-2-oxo-oxazolidin-5-yl)-2-methyl-propionic acid
  参考文献：
  名称：

  A short stereocontrolled synthesis of hydroxyethylene dipeptide isosteres

  摘要：

  A stereocontrolled synthesis of protected hydroxyethylene dipeptide isosteres 14 and 16 is described. It provides the 2R,4S,5S epimers required for the preparation of aspartic proteinase inhibitors. The choice of a benzene ring as a precursor to the carboxylic acid function has enabled us to use the readily accessible chiral Grignard reagent 3 which reacts with the protected alpha-amino aldehyde 8 stereoselectively. Kilogram quantities of 16 have been produced by this route in a satisfactory overall yield. The combination of N- and 0-protecting groups employed facilitates the incorporation of 14 or 16 into peptide-based enzyme inhibitors.

  DOI：

  10.1021/jo00060a052

文献信息

• A short stereocontrolled synthesis of hydroxyethylene dipeptide isosteres
  作者：D. Michael Jones、Bo Nilsson、Michael Szelke

  DOI：10.1021/jo00060a052

  日期：1993.4

  A stereocontrolled synthesis of protected hydroxyethylene dipeptide isosteres 14 and 16 is described. It provides the 2R,4S,5S epimers required for the preparation of aspartic proteinase inhibitors. The choice of a benzene ring as a precursor to the carboxylic acid function has enabled us to use the readily accessible chiral Grignard reagent 3 which reacts with the protected alpha-amino aldehyde 8 stereoselectively. Kilogram quantities of 16 have been produced by this route in a satisfactory overall yield. The combination of N- and 0-protecting groups employed facilitates the incorporation of 14 or 16 into peptide-based enzyme inhibitors.