(2S,3S)-3-(1-Benzyl-1H-imidazol-4-yl)-2-tert-butoxycarbonylamino-butyric acid | 409102-44-9

• 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: (2S,3S)-3-(1-Benzyl-1H-imidazol-4-yl)-2-tert-butoxycarbonylamino-butyric acid
• CAS: 409102-44-9
• 化学式: C₁₉H₂₅N₃O₄
• 分子量: 359.425
• InChiKey: BXZINUZAMVOALC-CJNGLKHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  93.45
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-Pyrrolidine-2-carboxylic acid [(R)-2,2-dimethyl-1-((S)-1-naphthalen-1-yl-ethylcarbamoyl)-propyl]-amide 、 (2S,3S)-3-(1-Benzyl-1H-imidazol-4-yl)-2-tert-butoxycarbonylamino-butyric acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 生成 tert-butyl N-[(2S,3S)-3-(1-benzylimidazol-4-yl)-1-[(2S)-2-[[(2R)-3,3-dimethyl-1-[[(1S)-1-naphthalen-1-ylethyl]amino]-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  Asymmetric Azidation−Cycloaddition with Open-Chain Peptide-Based Catalysts. A Sequential Enantioselective Route to Triazoles

  摘要：

  A family of beta-substituted histidine-containing peptides has been synthesized to probe the effect of noncovalent conformational rigidification on catalyst enantioselectivity. Unambiguous enhancement of enantioselectivity in the conjugate addition of azide to alpha,beta-unsaturated carboxylate derivatives has been achieved, enabling application to a sequential asymmetric azidation/cycloaddition for the synthesis of optically enriched triazoles and triazolines.

  DOI：

  10.1021/ja0177814
• 作为产物：
  描述：

  (S)-3-[(2S,3S)-2-Azido-3-(1-benzyl-1H-imidazol-4-yl)-butyryl]-4-phenyl-oxazolidin-2-one 在 palladium on activated charcoal lithium hydroxide 、 氢气 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 21.5h， 生成 (2S,3S)-3-(1-Benzyl-1H-imidazol-4-yl)-2-tert-butoxycarbonylamino-butyric acid
  参考文献：
  名称：

  Asymmetric Azidation−Cycloaddition with Open-Chain Peptide-Based Catalysts. A Sequential Enantioselective Route to Triazoles

  摘要：

  A family of beta-substituted histidine-containing peptides has been synthesized to probe the effect of noncovalent conformational rigidification on catalyst enantioselectivity. Unambiguous enhancement of enantioselectivity in the conjugate addition of azide to alpha,beta-unsaturated carboxylate derivatives has been achieved, enabling application to a sequential asymmetric azidation/cycloaddition for the synthesis of optically enriched triazoles and triazolines.

  DOI：

  10.1021/ja0177814