Cycloα-methyl-N^ω,N^ω'-bis(benzyloxycarbonyl)-L-arginylglycyl> | 160881-06-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Cycloα-methyl-N^ω,N^ω'-bis(benzyloxycarbonyl)-L-arginylglycyl>
• 英文别名: Cyclo[L-aspartyl-3-(aminomethyl)benzoyl-D-(2-aminobutyryl)-N^α-methyl-N^ω,N^ω'-bis(benzyloxycarbonyl)-L-arginylglycyl]；2-[(5S,11S,14R)-11-[3-[bis(phenylmethoxycarbonylamino)methylideneamino]propyl]-14-ethyl-12-methyl-4,7,10,13,16-pentaoxo-3,6,9,12,15-pentazabicyclo[15.3.1]henicosa-1(21),17,19-trien-5-yl]acetic acid
• CAS: 160881-06-1
• 化学式: C₄₁H₄₈N₈O₁₁
• 分子量: 828.879
• InChiKey: WSCJEGMSJVQKAI-RTOKGZNSSA-N

物化性质

• 密度：
  1.366±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  60
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  263
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  溴甲基乙酸酯 、 Cycloα-methyl-N^ω,N^ω'-bis(benzyloxycarbonyl)-L-arginylglycyl> 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 acetyloxymethyl 2-[(5S,11S,14R)-11-[3-[bis(phenylmethoxycarbonylamino)methylideneamino]propyl]-14-ethyl-12-methyl-4,7,10,13,16-pentaoxo-3,6,9,12,15-pentazabicyclo[15.3.1]henicosa-1(21),17,19-trien-5-yl]acetate
  参考文献：
  名称：

  An Efficient Synthesis of Glycoprotein IIb/IIIa Inhibitor DMP728. A Novel Synthesis of N.alpha.-Methylarginine-Containing Peptide

  摘要：

  An efficient synthesis of an antithrombotic cyclic peptide antagonist of glycoprotein IIb/IIIa, cycle(D-Abu-N-a-methyl-Arg-Gly-Asp-m-(aminomethyl)benzoic acid) has been developed. In the course of this work an efficient and selective method has been developed for the synthesis of derivatives of N-a-methylarginine from Cbz-Gln. The carboxamide of Cbz-Gln is dehydrated to the corresponding nitrile, and the resulting compound is methylated providing Cbz-2-(methylamino)-4-cyanobutyric acid, a diprotected precursor of N-a-methylornithine. At a later point in the reaction sequence the nitrile is reduced to the amine and the resulting N-a-methylornithine derivative is guanylated, converting it to a derivative of N-a-methylarginine.

  DOI：

  10.1021/jo00109a027
• 作为产物：
  描述：

  Cycloα-methyl-N^ω,N^ω'-bis(benzyloxycarbonyl)-L-arginylglycyl> 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以97%的产率得到Cycloα-methyl-N^ω,N^ω'-bis(benzyloxycarbonyl)-L-arginylglycyl>
  参考文献：
  名称：

  An Efficient Synthesis of Glycoprotein IIb/IIIa Inhibitor DMP728. A Novel Synthesis of N.alpha.-Methylarginine-Containing Peptide

  摘要：

  An efficient synthesis of an antithrombotic cyclic peptide antagonist of glycoprotein IIb/IIIa, cycle(D-Abu-N-a-methyl-Arg-Gly-Asp-m-(aminomethyl)benzoic acid) has been developed. In the course of this work an efficient and selective method has been developed for the synthesis of derivatives of N-a-methylarginine from Cbz-Gln. The carboxamide of Cbz-Gln is dehydrated to the corresponding nitrile, and the resulting compound is methylated providing Cbz-2-(methylamino)-4-cyanobutyric acid, a diprotected precursor of N-a-methylornithine. At a later point in the reaction sequence the nitrile is reduced to the amine and the resulting N-a-methylornithine derivative is guanylated, converting it to a derivative of N-a-methylarginine.

  DOI：

  10.1021/jo00109a027

文献信息

• An Efficient Synthesis of Glycoprotein IIb/IIIa Inhibitor DMP728. A Novel Synthesis of N.alpha.-Methylarginine-Containing Peptide
  作者：Chu-Biao Xue、William F. DeGrado

  DOI：10.1021/jo00109a027

  日期：1995.2

  An efficient synthesis of an antithrombotic cyclic peptide antagonist of glycoprotein IIb/IIIa, cycle(D-Abu-N-a-methyl-Arg-Gly-Asp-m-(aminomethyl)benzoic acid) has been developed. In the course of this work an efficient and selective method has been developed for the synthesis of derivatives of N-a-methylarginine from Cbz-Gln. The carboxamide of Cbz-Gln is dehydrated to the corresponding nitrile, and the resulting compound is methylated providing Cbz-2-(methylamino)-4-cyanobutyric acid, a diprotected precursor of N-a-methylornithine. At a later point in the reaction sequence the nitrile is reduced to the amine and the resulting N-a-methylornithine derivative is guanylated, converting it to a derivative of N-a-methylarginine.