D-(-)-N-<(1,1-dimethylethoxy)carbonyl>-4-chlorophenylalanine 2-bromoethyl ester | 139377-30-3

• 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: D-(-)-N-<(1,1-dimethylethoxy)carbonyl>-4-chlorophenylalanine 2-bromoethyl ester
• 英文别名: D-(-)-N-[(1,1-dimethylethoxy)carbonyl]-4-chlorophenylalanine 2-bromoethyl ester；2-bromoethyl (2R)-3-(4-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 139377-30-3
• 化学式: C₁₆H₂₁BrClNO₄
• 分子量: 406.704
• InChiKey: YLGABEHPSNBFGO-CYBMUJFWSA-N

物化性质

• 沸点：
  497.2±45.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  D-(-)-N-<(1,1-dimethylethoxy)carbonyl>-4-chlorophenylalanine 2-bromoethyl ester 在 palladium on activated charcoal 1,3-环己二烯 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 D-N-<(1,1-dimethylethoxy)carbonyl>-O--2-oxo-2-ethoxyethyl>phenyl>tyrosine
  参考文献：
  名称：

  Model studies on the synthesis of carboxylate-binding pocket analogs of vancomycin using arene-ruthenium chemistry

  摘要：

  Preparation of several protected (D)-chlorophenylalanine derivatives in high optical purity and their complex formation with the [RuCp]+ moiety are described. The complexation reaction, as well as subsequent photochemical decomplexations, proceeds with retention of optical purity. Reactions of these chloroarene complexes with 3-hydroxyphenylglycine derivatives proceed under mild conditions to give aryl ether-ruthenium complexes, which can be converted to diaryl ethers in which both aromatic rings have protected amino acid or peptide side chains. Efforts to effect cycloamidation to give vancomycin carboxylate-binding pocket analogues, using a number of known coupling reagents, were unsuccessful.

  DOI：

  10.1021/jo00032a028
• 作为产物：
  描述：

  3-(4-氯苯基)丙酸 在 palladium on activated charcoal 吡啶 、 lithium hydroxide 、 正丁基锂 、 2,4,6-三异丙基苯磺酰叠氮化物 、 氢气 、 双氧水 、 双(三甲基硅烷基)氨基钾 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 19.2h， 生成 D-(-)-N-<(1,1-dimethylethoxy)carbonyl>-4-chlorophenylalanine 2-bromoethyl ester
  参考文献：
  名称：

  Model studies on the synthesis of carboxylate-binding pocket analogs of vancomycin using arene-ruthenium chemistry

  摘要：

  Preparation of several protected (D)-chlorophenylalanine derivatives in high optical purity and their complex formation with the [RuCp]+ moiety are described. The complexation reaction, as well as subsequent photochemical decomplexations, proceeds with retention of optical purity. Reactions of these chloroarene complexes with 3-hydroxyphenylglycine derivatives proceed under mild conditions to give aryl ether-ruthenium complexes, which can be converted to diaryl ethers in which both aromatic rings have protected amino acid or peptide side chains. Efforts to effect cycloamidation to give vancomycin carboxylate-binding pocket analogues, using a number of known coupling reagents, were unsuccessful.

  DOI：

  10.1021/jo00032a028

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.
• Model studies on the synthesis of carboxylate-binding pocket analogs of vancomycin using arene-ruthenium chemistry
  作者：Anthony J. Pearson、Jewn G. Park

  DOI：10.1021/jo00032a028

  日期：1992.3

  Preparation of several protected (D)-chlorophenylalanine derivatives in high optical purity and their complex formation with the [RuCp]+ moiety are described. The complexation reaction, as well as subsequent photochemical decomplexations, proceeds with retention of optical purity. Reactions of these chloroarene complexes with 3-hydroxyphenylglycine derivatives proceed under mild conditions to give aryl ether-ruthenium complexes, which can be converted to diaryl ethers in which both aromatic rings have protected amino acid or peptide side chains. Efforts to effect cycloamidation to give vancomycin carboxylate-binding pocket analogues, using a number of known coupling reagents, were unsuccessful.