benzyl (2S)-3-phenyl-2-(tert-butyloxymethyl)propyl ether | 347851-54-1

• 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: benzyl (2S)-3-phenyl-2-(tert-butyloxymethyl)propyl ether
• 英文别名: [(2R)-2-benzyl-3-[(2-methylpropan-2-yl)oxy]propoxy]methylbenzene
• CAS: 347851-54-1
• 化学式: C₂₁H₂₈O₂
• 分子量: 312.452
• InChiKey: AWZFEEZAOGRJFZ-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl (2S)-3-phenyl-2-(tert-butyloxymethyl)propyl ether 在 palladium on activated charcoal 、 四丙基高钌酸铵 sodium tetrahydroborate 、 4 A molecular sieve 、 氢气 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 76.5h， 生成 tert-butyl (2R,5R,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：

  (S)-4-苄基-3-(3-苯基丙酰基)噁唑烷丁-2-酮 在 甲醇 、 锂硼氢 、 三氟化硼乙醚 、 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 38.0h， 生成 benzyl (2S)-3-phenyl-2-(tert-butyloxymethyl)propyl 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.