tert-butyl (2R,5S,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-7-phenyl-3-hepten-5-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: tert-butyl (2R,5S,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-7-phenyl-3-hepten-5-ol
• 英文别名: benzyl N-[(E,2S,3S,6R)-6-benzyl-3-hydroxy-7-[(2-methylpropan-2-yl)oxy]-1-phenylhept-4-en-2-yl]carbamate
• 化学式: C₃₂H₃₉NO₄
• 分子量: 501.666
• InChiKey: YOWVHUPDVPNSKX-BZWVIUAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-4-苄基-3-(3-苯基丙酰基)噁唑烷丁-2-酮 在 palladium on activated charcoal 、 四丙基高钌酸铵 甲醇 、 sodium tetrahydroborate 、 锂硼氢 、 4 A molecular sieve 、 三氟化硼乙醚 、 氢气 、 四氯化钛 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 环己烷 、 乙腈 为溶剂， 反应 114.5h， 生成 tert-butyl (2R,5S,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-7-phenyl-3-hepten-5-ol
  参考文献：
  名称：

  Design and Synthesis of a Conformationally Restricted Trans Peptide Isostere Based on the Bioactive Conformations of Saquinavir and Nelfinavir

  摘要：

  The design and synthesis of a new peptide isostere which contains a trans alkene core is described. The key step involves a Wadsworth-Emmons reaction between chiral aldehyde (2S)-9a and chiral phosphonate 7 under base-sensitive conditions to give a chiral enone (2R)-24a which was reduced to afford the desired trans alkene isosteres (2R,5R)-6a and (2R:5S)-6b (Scheme 6). A potential application of this isostere in the synthesis of HIV protease inhibitors is also discussed.

  DOI：

  10.1021/jo0016834

文献信息

• Design and Synthesis of a Conformationally Restricted Trans Peptide Isostere Based on the Bioactive Conformations of Saquinavir and Nelfinavir
  作者：Michael K. Edmonds、Andrew D. Abell

  DOI：10.1021/jo0016834

  日期：2001.6.1

  The design and synthesis of a new peptide isostere which contains a trans alkene core is described. The key step involves a Wadsworth-Emmons reaction between chiral aldehyde (2S)-9a and chiral phosphonate 7 under base-sensitive conditions to give a chiral enone (2R)-24a which was reduced to afford the desired trans alkene isosteres (2R,5R)-6a and (2R:5S)-6b (Scheme 6). A potential application of this isostere in the synthesis of HIV protease inhibitors is also discussed.