4-{(adamantan-1-yloxy)-[2-(2-oxo-2-phenyl-ethoxycarbonyl)-3-phenyl-propyl]-phosphinoyl}-4-(9H-fluoren-9-yl-methoxycarbonylamino)-butyric acid methyl ester | 918950-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 4-{(adamantan-1-yloxy)-[2-(2-oxo-2-phenyl-ethoxycarbonyl)-3-phenyl-propyl]-phosphinoyl}-4-(9H-fluoren-9-yl-methoxycarbonylamino)-butyric acid methyl ester
• 英文别名: methyl 4-[1-adamantyloxy-(2-benzyl-3-oxo-3-phenacyloxypropyl)phosphoryl]-4-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate
• CAS: 918950-06-8
• 化学式: C₄₈H₅₂NO₉P
• 分子量: 817.916
• InChiKey: NRXXNBNKJPGTHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  59
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-{(adamantan-1-yloxy)-[2-(2-oxo-2-phenyl-ethoxycarbonyl)-3-phenyl-propyl]-phosphinoyl}-4-(9H-fluoren-9-yl-methoxycarbonylamino)-butyric acid methyl ester 在 magnesium 、 溶剂黄146 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以83%的产率得到4-[(adamantan-1-yloxy)-(2-carboxy-3-phenyl-propyl)-phosphinoyl]-4-(9H-fluoren-9-yl-methoxycarbonylamino)-butyric acid methyl acid
  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
• 作为产物：
  描述：

  4-(9H-fluoren-9-yl-methoxycarbonylamino)-4-{(2-oxo-2-phenyl-ethoxy)-[2-(2-oxo-2-phenyl-ethoxycarbonyl)-3-phenyl-propyl]-phosphinoyl}-butyric acid methyl ester 在 三氟乙酸 、 silver(l) oxide 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 24.0h， 生成 4-{(adamantan-1-yloxy)-[2-(2-oxo-2-phenyl-ethoxycarbonyl)-3-phenyl-propyl]-phosphinoyl}-4-(9H-fluoren-9-yl-methoxycarbonylamino)-butyric acid methyl 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).