3-{(adamantan-1-yloxy)-[2-benzyloxy-1-(9H-fluoren-9-yl-methoxycarbonylamino)-ethyl]-phosphinoyl}-2-benzyl-propionic acid 2-oxo-2-phenyl-ethyl ester | 918950-10-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 3-{(adamantan-1-yloxy)-[2-benzyloxy-1-(9H-fluoren-9-yl-methoxycarbonylamino)-ethyl]-phosphinoyl}-2-benzyl-propionic acid 2-oxo-2-phenyl-ethyl ester
• 英文别名: phenacyl 2-[[1-adamantyloxy-[1-(9H-fluoren-9-ylmethoxycarbonylamino)-2-phenylmethoxyethyl]phosphoryl]methyl]-3-phenylpropanoate
• CAS: 918950-10-4
• 化学式: C₅₂H₅₄NO₈P
• 分子量: 851.976
• InChiKey: IQLVUAGHKPHMHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  62
• 可旋转键数：
  20
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-{(adamantan-1-yloxy)-[2-benzyloxy-1-(9H-fluoren-9-yl-methoxycarbonylamino)-ethyl]-phosphinoyl}-2-benzyl-propionic acid 2-oxo-2-phenyl-ethyl 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87%的产率得到3-{(adamantan-1-yloxy)-[2-benzyloxy-1-(9H-fluoren-9-yl-methoxycarbonylamino)-ethyl]-phosphinoyl}-2-benzyl-propionic 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：

  2-benzyl-3-{[2-benzyloxy-1-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-hydroxy-phosphinoyl}-propionic acid 在 三乙胺 、 三氟乙酸 、 silver(l) oxide 作用下， 以 二氯甲烷 、 氯仿 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 3-{(adamantan-1-yloxy)-[2-benzyloxy-1-(9H-fluoren-9-yl-methoxycarbonylamino)-ethyl]-phosphinoyl}-2-benzyl-propionic 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).