N-Boc-D-(2-aminobutyryl)-N^α-methyl-N^ω,N^ω'-bis(benzyloxycarbonyl)-L-arginylglycine tert-butyl ester

• 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: N-Boc-D-(2-aminobutyryl)-N^α-methyl-N^ω,N^ω'-bis(benzyloxycarbonyl)-L-arginylglycine tert-butyl ester
• 英文别名: tert-butyl 2-[[(2S)-5-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-[methyl-[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]pentanoyl]amino]acetate
• 化学式: C₃₈H₅₄N₆O₁₀
• 分子量: 754.881
• InChiKey: KEKFHQOZOAXRCE-WDYNHAJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  54
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  203
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-Boc-D-(2-aminobutyryl)-N^α-methyl-N^ω,N^ω'-bis(benzyloxycarbonyl)-L-arginylglycine tert-butyl ester 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 2.0h， 以99%的产率得到D-(2-Aminobutyryl)-N^α-methyl-N^ω,N^ω'-bis(benzyloxycarbonyl)-L-arginylglycine trifluoroacetic acid salt
  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：

  1,3-二(苄氧羰基)-2-甲基异硫脲 、 Boc-D-Abu-N(Me)Orn-Gly-OtBu 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-Boc-D-(2-aminobutyryl)-N^α-methyl-N^ω,N^ω'-bis(benzyloxycarbonyl)-L-arginylglycine tert-butyl ester
  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.