5-[benzyl-(2-oxo-2-phenyl-ethoxy)-phosphinoyl]-pentanoic acid 2-oxo-2-phenyl-ethyl ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[benzyl-(2-oxo-2-phenyl-ethoxy)-phosphinoyl]-pentanoic acid 2-oxo-2-phenyl-ethyl ester
• 英文别名: Phenacyl 5-[benzyl(phenacyloxy)phosphoryl]pentanoate
• 化学式: C₂₈H₂₉O₆P
• 分子量: 492.508
• InChiKey: RGVDGYDUKLKKLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-戊烯酸 在 palladium on activated charcoal 三甲基氯硅烷 、 次磷酸铵 、 三乙基硼 、 氢气 、 甲基三辛基氯化铵 、 碳酸氢钠 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 105.0h， 生成 5-[benzyl-(2-oxo-2-phenyl-ethoxy)-phosphinoyl]-pentanoic acid 2-oxo-2-phenyl-ethyl ester
  参考文献：
  名称：

  Chemoselective Protection of Solid-Phase Compatible Fmoc-Phosphinic Building Blocks

  摘要：

  An efficient four-step synthetic strategy able to fully discriminate hydroxyphosphinyl and carboxylic groups of Fmoc-phosphinic building blocks and related analogues has been developed. The proposed method applies selective acidic removal of the phenacyl (Pac) group from the hydroxyphosphinyl functionality and protection by the 1-adamantyl (Ad) group. Reductive removal of the Pac group from the carboxylic functionality leads to Fmoc-protected phosphinic pseudodipeptidic units suitable for phosphinic peptide and library development using solid-phase peptide synthesis (SPPS).

  DOI：

  10.1021/jo061535z

文献信息

• Chemoselective Protection of Solid-Phase Compatible Fmoc-Phosphinic Building Blocks
  作者：Magdalini Nasopoulou、Magdalini Matziari、Vincent Dive、Athanasios Yiotakis

  DOI：10.1021/jo061535z

  日期：2006.12.1

  An efficient four-step synthetic strategy able to fully discriminate hydroxyphosphinyl and carboxylic groups of Fmoc-phosphinic building blocks and related analogues has been developed. The proposed method applies selective acidic removal of the phenacyl (Pac) group from the hydroxyphosphinyl functionality and protection by the 1-adamantyl (Ad) group. Reductive removal of the Pac group from the carboxylic functionality leads to Fmoc-protected phosphinic pseudodipeptidic units suitable for phosphinic peptide and library development using solid-phase peptide synthesis (SPPS).