4-[(2-carboxy-3-phenyl-propyl)-hydroxy-phosphinoyl]-4-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid methyl ester | 865703-18-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 4-[(2-carboxy-3-phenyl-propyl)-hydroxy-phosphinoyl]-4-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid methyl ester
• 英文别名: 2-benzyl-3-[[1-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methoxy-4-oxobutyl]-hydroxyphosphoryl]propanoic acid
• CAS: 865703-18-0
• 化学式: C₃₀H₃₂NO₈P
• 分子量: 565.56
• InChiKey: CENVOTISRKMDGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-[(2-carboxy-3-phenyl-propyl)-hydroxy-phosphinoyl]-4-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid methyl ester 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 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
• 作为产物：
  描述：

  乙基2-苄基丙烯酸酯 在 sodium hydroxide 、 二(三甲基硅烷基)亚膦酸酯 、 溶剂黄146 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 30.0h， 生成 4-[(2-carboxy-3-phenyl-propyl)-hydroxy-phosphinoyl]-4-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid methyl ester
  参考文献：
  名称：

  Shortcut to Fmoc-Protected Phosphinic Pseudodipeptidic Blocks

  摘要：

  A three-component condensation reaction of Fmoc-carbamate, aldehydes, and alkylphosphinic acids provides a new, direct, and efficient method for synthesizing Fmoc-protected phosphinic pseudodipeptidic blocks, directly usable for solid-phase peptide synthesis.

  DOI：

  10.1021/ol051622y

文献信息

• Shortcut to Fmoc-Protected Phosphinic Pseudodipeptidic Blocks
  作者：Magdalini Matziari、Athanasios Yiotakis

  DOI：10.1021/ol051622y

  日期：2005.9.1

  A three-component condensation reaction of Fmoc-carbamate, aldehydes, and alkylphosphinic acids provides a new, direct, and efficient method for synthesizing Fmoc-protected phosphinic pseudodipeptidic blocks, directly usable for solid-phase peptide synthesis.
• 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).