(R)-4-<2-Methoxy-5-<1--L-(4-methoxyphenyl)glycinyl>amino>-2-ethoxy-2-oxoethyl>phenoxy>-N-<(1,1-dimethylethoxy)carbonyl>-D-phenylalanine | 169176-66-3

• 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: (R)-4-<2-Methoxy-5-<1--L-(4-methoxyphenyl)glycinyl>amino>-2-ethoxy-2-oxoethyl>phenoxy>-N-<(1,1-dimethylethoxy)carbonyl>-D-phenylalanine
• 英文别名: (2R)-3-[4-[5-[(1R)-2-ethoxy-1-[[(2S)-2-(4-methoxyphenyl)-2-(phenylmethoxycarbonylamino)acetyl]amino]-2-oxoethyl]-2-methoxyphenoxy]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 169176-66-3
• 化学式: C₄₂H₄₇N₃O₁₂
• 分子量: 785.848
• InChiKey: AUOTWUQQOSMMKU-RZKSILPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  57
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  197
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (R)-4-<2-Methoxy-5-<1--L-(4-methoxyphenyl)glycinyl>amino>-2-ethoxy-2-oxoethyl>phenoxy>-N-<(1,1-dimethylethoxy)carbonyl>-D-phenylalanine 在 palladium on activated charcoal 盐酸 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、98.06 kPa 条件下， 反应 18.0h， 生成 (1R,2R)-amino>-3-oxo-3-(pentafluorophenoxy)propyl>phenoxy>-4-methoxyphenyl>-2-ethoxy-2-oxoethyl>amino>-(S)-(4-methoxyphenyl)glycine hydrochloride
  参考文献：
  名称：

  Synthesis of a 16-Membered Cyclic Peptide Model of the BCF Rings of Ristocetin A Using Arene-Ruthenium Chemistry Coupled with Cycloamidation

  摘要：

  A convergent synthetic approach to the cyclic peptide 4, which is a model for the B/C/F ring system of ristocetin B, is described. A key reaction is the coupling of the phenolic dipeptide 5, constructed from arylglycine subunits, with the chlorophenylalanine-RuCp cationic complex 6, followed by demetalation of the product to give the diaryl ether 7, without epimerization at any of the amino acid residues. Deprotection of 7 followed by cycloamidation affords the target molecule 4, produced as a mixture of atropdiastereomers which were separated and characterized by NMR spectroscopy.

  DOI：

  10.1021/jo00127a020
• 作为产物：
  描述：

  对甲氧基苯乙酸 在 palladium on activated charcoal 盐酸 、 N,N-二甲基丙烯基脲 、 lithium hydroxide 、 正丁基锂 、 samarium diiodide 、 2,4,6-三异丙基苯磺酰叠氮化物 、 氢气 、 双(三甲基硅烷基)氨基钾 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， -78.0~25.0 ℃ 、98.06 kPa 条件下， 反应 62.78h， 生成 (R)-4-<2-Methoxy-5-<1--L-(4-methoxyphenyl)glycinyl>amino>-2-ethoxy-2-oxoethyl>phenoxy>-N-<(1,1-dimethylethoxy)carbonyl>-D-phenylalanine
  参考文献：
  名称：

  Synthesis of a 16-Membered Cyclic Peptide Model of the BCF Rings of Ristocetin A Using Arene-Ruthenium Chemistry Coupled with Cycloamidation

  摘要：

  A convergent synthetic approach to the cyclic peptide 4, which is a model for the B/C/F ring system of ristocetin B, is described. A key reaction is the coupling of the phenolic dipeptide 5, constructed from arylglycine subunits, with the chlorophenylalanine-RuCp cationic complex 6, followed by demetalation of the product to give the diaryl ether 7, without epimerization at any of the amino acid residues. Deprotection of 7 followed by cycloamidation affords the target molecule 4, produced as a mixture of atropdiastereomers which were separated and characterized by NMR spectroscopy.

  DOI：

  10.1021/jo00127a020

文献信息

• Synthesis of a 16-Membered Cyclic Peptide Model of the BCF Rings of Ristocetin A Using Arene-Ruthenium Chemistry Coupled with Cycloamidation
  作者：Anthony J. Pearson、Kieseung Lee

  DOI：10.1021/jo00127a020

  日期：1995.11

  A convergent synthetic approach to the cyclic peptide 4, which is a model for the B/C/F ring system of ristocetin B, is described. A key reaction is the coupling of the phenolic dipeptide 5, constructed from arylglycine subunits, with the chlorophenylalanine-RuCp cationic complex 6, followed by demetalation of the product to give the diaryl ether 7, without epimerization at any of the amino acid residues. Deprotection of 7 followed by cycloamidation affords the target molecule 4, produced as a mixture of atropdiastereomers which were separated and characterized by NMR spectroscopy.