benzyl (3S)-5-bromo-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxopentanoate | 350606-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: benzyl (3S)-5-bromo-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxopentanoate
• CAS: 350606-06-3
• 化学式: C₂₇H₂₄BrNO₅
• 分子量: 522.395
• InChiKey: BFGSLOQBTFTLJM-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (3S)-5-bromo-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxopentanoate 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 以82%的产率得到Fmoc-Asp(β-Bzl)-CH2N3
  参考文献：
  名称：

  Peptidomimetics Through Click Chemistry: Synthesis of Novel β-Keto Triazole Acids from N-Protected Amino Acids

  摘要：

  描述了一种有效的程序，用于从N-氨基甲酸酯保护的氨基酸制备叠氮甲基酮及其在铜(I)催化的叠氮-炔烃环加成反应中的应用。该合成在温和条件下进行，适用于所有常用的氨基甲酸酯保护的氨基酸（Fmoc、Boc 和 Z），并以良好的产率获得了所需的叠氮化物/三唑化物。还展示了将这些三唑氨基酸纳入小肽中，生成含有β-酮三唑单元的二肽模仿物。

  DOI：

  10.1007/s10989-010-9214-z
• 作为产物：
  描述：

  芴甲氧羰基-天冬氨酸-β苄脂 在 氢溴酸 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 benzyl (3S)-5-bromo-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxopentanoate
  参考文献：
  名称：

  Synthesis of N-Urethane Protected α-Aminoalkyl-α′-cyanomethyl Ketones; Application to the Synthesis of 3-Substituted 5-Amino-1H-pyrazole Tethered Peptidomimetics

  摘要：

  The preparation of N-protected amino/peptide alpha-cyanomethyl ketones through cyanation of the corresponding alpha-bromomethyl ketones is described. The utility of the resulting acyanomethyl ketones in the synthesis of 3-substituted-5-amino-1H-pyrazoles has also been demonstrated. In both steps a wide range of N-protected amino/peptide acids has been employed and the products are obtained in good yield. The enantiomeric purity of both the alpha-cyanomethyl ketones and pyrazoles were confirmed by chiral HPLC analysis of the corresponding Z-protected D-and L-Ala-OH as model substrates. The synthesis of peptide pyrazolecarbox-amides is also delineated.

  DOI：

  10.1055/s-0032-1316586

文献信息

• Peptidomimetics Through Click Chemistry: Synthesis of Novel β-Keto Triazole Acids from N-Protected Amino Acids
  作者：N. Narendra、T. M. Vishwanatha、Vommina V. Sureshbabu

  DOI：10.1007/s10989-010-9214-z

  日期：2010.12

  An efficient procedure for the preparation of azidomethylketones from N-urethane protected amino acids and their application in Cu(I) catalyzed azide-alkyne cycloaddition reaction are described. The synthesis has been carried out under mild conditions with all the commonly used urethane protected (Fmoc, Boc and Z) amino acids and the desired azides/triazoles were obtained in good yields. Incorporation of these triazole amino acids into small peptides generating dipeptidomimetics containing β-keto triazole units has also been demonstrated.

  描述了一种有效的程序，用于从N-氨基甲酸酯保护的氨基酸制备叠氮甲基酮及其在铜(I)催化的叠氮-炔烃环加成反应中的应用。该合成在温和条件下进行，适用于所有常用的氨基甲酸酯保护的氨基酸（Fmoc、Boc 和 Z），并以良好的产率获得了所需的叠氮化物/三唑化物。还展示了将这些三唑氨基酸纳入小肽中，生成含有β-酮三唑单元的二肽模仿物。
• Synthesis of N-Urethane Protected α-Aminoalkyl-α′-cyanomethyl Ketones; Application to the Synthesis of 3-Substituted 5-Amino-1H-pyrazole Tethered Peptidomimetics
  作者：Vommina Sureshbabu、M. Sharnabai、G. Nagendra

  DOI：10.1055/s-0032-1316586

  日期：2012.8

  The preparation of N-protected amino/peptide alpha-cyanomethyl ketones through cyanation of the corresponding alpha-bromomethyl ketones is described. The utility of the resulting acyanomethyl ketones in the synthesis of 3-substituted-5-amino-1H-pyrazoles has also been demonstrated. In both steps a wide range of N-protected amino/peptide acids has been employed and the products are obtained in good yield. The enantiomeric purity of both the alpha-cyanomethyl ketones and pyrazoles were confirmed by chiral HPLC analysis of the corresponding Z-protected D-and L-Ala-OH as model substrates. The synthesis of peptide pyrazolecarbox-amides is also delineated.