benzyl (2S)-2-[[(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(phenylmethoxycarbonylamino)pentanoyl]oxybutanoyl]amino]-4-methylpentanoate | 373605-00-6

• 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: benzyl (2S)-2-[[(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(phenylmethoxycarbonylamino)pentanoyl]oxybutanoyl]amino]-4-methylpentanoate
• CAS: 373605-00-6
• 化学式: C₅₀H₆₀N₄O₁₁
• 分子量: 893.047
• InChiKey: NTVWAQLEDYRUPT-LMNFPSAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  65
• 可旋转键数：
  26
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  197
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  benzyl (2S)-2-[[(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(phenylmethoxycarbonylamino)pentanoyl]oxybutanoyl]amino]-4-methylpentanoate 在 二乙胺 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到(S)-2-[(S)-3-((S)-5-Amino-2-tert-butoxycarbonylamino-pentanoylamino)-2-hydroxy-butyrylamino]-4-methyl-pentanoic acid benzyl ester
  参考文献：
  名称：

  Concise total synthesis of the prolyl endopeptidase inhibitor eurystatin A via a novel Passerini reaction–deprotection–acyl migration strategy

  摘要：

  The Passerini reaction between suitably protected alaninal, leucine isonitrile, and ornithine components delivered adducts 10a,b in high yield. Orthogonal N-deprotection of 10a led, via a smooth O- to N-acyl migration, to 11, which constitutes the entire skeleton of the eurystatins. Subsequent deprotection, macrocyclization, elaboration, and final oxidation steps efficiently afforded eurystatin A 1a in high overall yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01287-4
• 作为产物：
  描述：

  N-Formyl-L-leucine benzyl ester 在 N-甲基吗啉 、 氯甲酸三氯甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 benzyl (2S)-2-[[(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(phenylmethoxycarbonylamino)pentanoyl]oxybutanoyl]amino]-4-methylpentanoate
  参考文献：
  名称：

  Concise total synthesis of the prolyl endopeptidase inhibitor eurystatin A via a novel Passerini reaction–deprotection–acyl migration strategy

  摘要：

  The Passerini reaction between suitably protected alaninal, leucine isonitrile, and ornithine components delivered adducts 10a,b in high yield. Orthogonal N-deprotection of 10a led, via a smooth O- to N-acyl migration, to 11, which constitutes the entire skeleton of the eurystatins. Subsequent deprotection, macrocyclization, elaboration, and final oxidation steps efficiently afforded eurystatin A 1a in high overall yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01287-4