3-[[1-(9H-fluoren-9-yl-methoxycarbonylamino)-3-methyl-butyl]-(2-oxo-2-phenyl-ethoxy)-phosphinoyl]-propionic acid 2-oxo-2-phenyl-ethyl ester | 918949-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 3-[[1-(9H-fluoren-9-yl-methoxycarbonylamino)-3-methyl-butyl]-(2-oxo-2-phenyl-ethoxy)-phosphinoyl]-propionic acid 2-oxo-2-phenyl-ethyl ester
• 英文别名: phenacyl 3-[[1-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutyl]-phenacyloxyphosphoryl]propanoate
• CAS: 918949-82-3
• 化学式: C₃₉H₄₀NO₈P
• 分子量: 681.722
• InChiKey: OBNANDSINHSNOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  49
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-[[1-(9H-fluoren-9-yl-methoxycarbonylamino)-3-methyl-butyl]-(2-oxo-2-phenyl-ethoxy)-phosphinoyl]-propionic acid 2-oxo-2-phenyl-ethyl 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 3-{(adamantan-1-yloxy)-[1-(9H-fluoren-9-yl-methoxycarbonylamino)-3-methyl-butyl]-phosphinoyl}-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
• 作为产物：
  描述：

  3-{[1-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyl]-hydroxy-phosphinoyl}-propionic acid 、 2-溴苯乙酮 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 以82%的产率得到3-[[1-(9H-fluoren-9-yl-methoxycarbonylamino)-3-methyl-butyl]-(2-oxo-2-phenyl-ethoxy)-phosphinoyl]-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).