(4S)-N-benzyl-3-oxo-N-phenyl-5-phenylmethoxy-4-(tritylamino)pentanamide | 1007843-15-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (4S)-N-benzyl-3-oxo-N-phenyl-5-phenylmethoxy-4-(tritylamino)pentanamide
• CAS: 1007843-15-3
• 化学式: C₄₄H₄₀N₂O₃
• 分子量: 644.813
• InChiKey: OTPOUVFSHHGZQA-RWYGWLOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-N-benzyl-3-oxo-N-phenyl-5-phenylmethoxy-4-(tritylamino)pentanamide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 甲烷磺酰基叠氮化物 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以89%的产率得到(4S)-N-benzyl-2-diazo-3-oxo-N-phenyl-5-phenylmethoxy-4-(tritylamino)pentanamide
  参考文献：
  名称：

  Structural Characterization of an Enantiomerically Pure Amino Acid Imidazolide and Direct Formation of the β-Lactam Nucleus from an α-Amino Acid

  摘要：

  Decomposition of a diazo beta-ketoamide derived from N-trityl serine imidazolide and N-protected acetanilides provides, instead of the expected beta-acyloxindole product, an enantiomerically pure (EP) beta-lactam. The amino acid stereocenter is incorporated, the second chiral center is induced, and trityl protection of the beta-lactam ring is realized for the first time. The desired beta-acyloxindole is obtained from oxindole and Tr-Ser(OBn)-imidazole, the X-ray of which provides the first structural determination of an EP amino acid imidazolide.

  DOI：

  10.1021/ol7025922
• 作为产物：
  描述：

  N-苄基-N-苯基乙酰胺 、 Tr-Ser(OBn)-Im 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以55%的产率得到(4S)-N-benzyl-3-oxo-N-phenyl-5-phenylmethoxy-4-(tritylamino)pentanamide
  参考文献：
  名称：

  Structural Characterization of an Enantiomerically Pure Amino Acid Imidazolide and Direct Formation of the β-Lactam Nucleus from an α-Amino Acid

  摘要：

  Decomposition of a diazo beta-ketoamide derived from N-trityl serine imidazolide and N-protected acetanilides provides, instead of the expected beta-acyloxindole product, an enantiomerically pure (EP) beta-lactam. The amino acid stereocenter is incorporated, the second chiral center is induced, and trityl protection of the beta-lactam ring is realized for the first time. The desired beta-acyloxindole is obtained from oxindole and Tr-Ser(OBn)-imidazole, the X-ray of which provides the first structural determination of an EP amino acid imidazolide.

  DOI：

  10.1021/ol7025922

文献信息

• Structural Characterization of an Enantiomerically Pure Amino Acid Imidazolide and Direct Formation of the β-Lactam Nucleus from an α-Amino Acid
  作者：Brian S. Gerstenberger、Jinzhen Lin、Yvette S. Mimieux、Lauren E. Brown、Allen G. Oliver、Joseph P. Konopelski

  DOI：10.1021/ol7025922

  日期：2008.2.1

  Decomposition of a diazo beta-ketoamide derived from N-trityl serine imidazolide and N-protected acetanilides provides, instead of the expected beta-acyloxindole product, an enantiomerically pure (EP) beta-lactam. The amino acid stereocenter is incorporated, the second chiral center is induced, and trityl protection of the beta-lactam ring is realized for the first time. The desired beta-acyloxindole is obtained from oxindole and Tr-Ser(OBn)-imidazole, the X-ray of which provides the first structural determination of an EP amino acid imidazolide.