(4S,5S)-4-(cyclohexylmethyl)-5-[(2R)-2-phenylpropyl]-1,3-oxazolidin-2-one | 147426-13-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5S)-4-(cyclohexylmethyl)-5-[(2R)-2-phenylpropyl]-1,3-oxazolidin-2-one
• CAS: 147426-13-9
• 化学式: C₁₉H₂₇NO₂
• 分子量: 301.429
• InChiKey: UGHDJGRQRPYOMS-JLSDUUJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-(cyclohexylmethyl)-5-[(2R)-2-phenylpropyl]-1,3-oxazolidin-2-one 在 sodium periodate 、 四氧化钌 、 红铝 作用下， 以 乙酸乙酯 为溶剂， 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：

  (S)-2-苯基-1-丙醇 在 吡啶 、 sodium hydride 、 magnesium 、 1,2-二溴乙烷 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 22.5h， 生成 (4S,5S)-4-(cyclohexylmethyl)-5-[(2R)-2-phenylpropyl]-1,3-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

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.