(2S,3S,5R)-2-amino-1-cyclohexyl-5-phenylhexan-3-ol | 197568-73-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,3S,5R)-2-amino-1-cyclohexyl-5-phenylhexan-3-ol
• CAS: 197568-73-3
• 化学式: C₁₈H₂₉NO
• 分子量: 275.434
• InChiKey: BMNZDASRIKUYEZ-JLSDUUJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S,5R)-2-amino-1-cyclohexyl-5-phenylhexan-3-ol 在 2,6-二甲基吡啶 、 sodium periodate 、 四氧化钌 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 (2R,4S,5S)-4-<(tert-butyldimethylsilyl)oxy>-6-cyclohexyl-2-methyl-5-<(2',2',2'-trichloro-1',1'-dimethylethoxycarbonyl)amino>hexanoic 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
• 作为产物：
  描述：

  S-2-苯基丙酸 在 吡啶 、 盐酸 、 magnesium 、 1,2-二溴乙烷 、 红铝 、 lithium bromide 作用下， 以 1,4-二氧六环 、 丙酮 、 甲苯 为溶剂， 反应 22.5h， 生成 (2S,3S,5R)-2-amino-1-cyclohexyl-5-phenylhexan-3-ol
  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