tert-butyldimethylsilyl-(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-heptenyl ether | 347851-56-3

• 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-butyldimethylsilyl-(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-heptenyl ether
• 英文别名: benzyl N-[(E,2S)-6-benzyl-7-[tert-butyl(dimethyl)silyl]oxy-3-oxo-1-phenylhept-4-en-2-yl]carbamate
• CAS: 347851-56-3
• 化学式: C₃₄H₄₃NO₄Si
• 分子量: 557.805
• InChiKey: FPNYGPOYPUNSPQ-RUCFFRAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.53
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl-(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-heptenyl ether 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 环己烷 、 水 为溶剂， 反应 88.5h， 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
• 作为产物：
  描述：

  2-苄基-3-羟基丙酸甲酯 在 咪唑 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 26.0h， 生成 tert-butyldimethylsilyl-(2RS,6S)-6-[N-(benzyloxycarbonyl)amino]-2-benzyl-5-oxo-7-phenyl-3-heptenyl ether
  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.