(2R,4S,5S)-5-<(tert-butyloxycarbonyl)amino>-6-cyclohexyl-4-hydroxy-2-phenylhexane | 147426-12-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,4S,5S)-5-<(tert-butyloxycarbonyl)amino>-6-cyclohexyl-4-hydroxy-2-phenylhexane
• 英文别名: (2R,4S,5S)-5-[(tert-butyloxycarbonyl)amino]-6-cyclohexyl-4-hydroxy-2-phenylhexane；tert-butyl N-[(2S,3S,5R)-1-cyclohexyl-3-hydroxy-5-phenylhexan-2-yl]carbamate
• CAS: 147426-12-8
• 化学式: C₂₃H₃₇NO₃
• 分子量: 375.552
• InChiKey: GNTBMONOVFBXPO-QMMLZNLJSA-N

物化性质

• 沸点：
  518.7±43.0 °C(predicted)
• 密度：
  1.029±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4S,5S)-5-<(tert-butyloxycarbonyl)amino>-6-cyclohexyl-4-hydroxy-2-phenylhexane 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (2R,4S,5S)-6-cyclohexyl-4-hydroxy-2-phenyl-5-<(2',2',2'-trichloro-1',1'-dimethylethoxycarbonyl)amino>hexane
  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 、 magnesium 、 1,2-二溴乙烷 、 lithium bromide 作用下， 以 丙酮 为溶剂， 反应 19.5h， 生成 (2R,4S,5S)-5-<(tert-butyloxycarbonyl)amino>-6-cyclohexyl-4-hydroxy-2-phenylhexane
  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