(2R,4S,5S)-4-<(tert-butyldimethylsilyl)oxy>-6-cyclohexyl-2-phenyl-5-<(2',2',2'-trichloro-1',1'-dimethylethoxycarbonyl)amino>hexane | 147426-15-1

• 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)-4-<(tert-butyldimethylsilyl)oxy>-6-cyclohexyl-2-phenyl-5-<(2',2',2'-trichloro-1',1'-dimethylethoxycarbonyl)amino>hexane
• 英文别名: (2R,4S,5S)-4-[(tert-butyldimethylsilyl)oxy]-6-cyclohexyl-2-phenyl-5-[(2',2',2'-trichloro-1',1'-dimethylethoxycarbonyl)amino]hexane；(1,1,1-trichloro-2-methylpropan-2-yl) N-[(2S,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-1-cyclohexyl-5-phenylhexan-2-yl]carbamate
• CAS: 147426-15-1
• 化学式: C₂₉H₄₈Cl₃NO₃Si
• 分子量: 593.15
• InChiKey: CVOXCFXPIPDQGF-ZODMCCGTSA-N

物化性质

• 沸点：
  598.7±50.0 °C(predicted)
• 密度：
  1.093±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.78
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4S,5S)-4-<(tert-butyldimethylsilyl)oxy>-6-cyclohexyl-2-phenyl-5-<(2',2',2'-trichloro-1',1'-dimethylethoxycarbonyl)amino>hexane 在 sodium periodate 、 四氧化钌 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以87%的产率得到(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-1-丙醇 在 吡啶 、 2,6-二甲基吡啶 、 盐酸 、 magnesium 、 1,2-二溴乙烷 、 三乙胺 、 lithium bromide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 丙酮 为溶剂， 反应 22.5h， 生成 (2R,4S,5S)-4-<(tert-butyldimethylsilyl)oxy>-6-cyclohexyl-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

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.