{2-[((S)-6-Benzyl-4-oxo-1,2,3,4,5,6,7,8-octahydro-[1,6]naphthyridine-2-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester | 1028295-08-0

• 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: {2-[((S)-6-Benzyl-4-oxo-1,2,3,4,5,6,7,8-octahydro-[1,6]naphthyridine-2-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-[[(2S)-6-benzyl-4-oxo-1,2,3,5,7,8-hexahydro-1,6-naphthyridine-2-carbonyl]amino]ethyl]carbamate
• CAS: 1028295-08-0
• 化学式: C₂₃H₃₂N₄O₄
• 分子量: 428.531
• InChiKey: HLMCLUCADTXKJY-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  99.8
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  {2-[((S)-6-Benzyl-4-oxo-1,2,3,4,5,6,7,8-octahydro-[1,6]naphthyridine-2-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 {2-[((S)-4-Oxo-1,2,3,4,5,6,7,8-octahydro-[1,6]naphthyridine-2-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design and Asymmetric Synthesis of β-Strand Peptidomimetics

  摘要：

  We describe the asymmetric synthesis of non-peptidic compounds that feature rigid backbone conformations and present various side-chain functions. The key step in the synthesis of these compounds is the C-acylation of an appropriate ketone with a suitably protected aspartic acid derivative. The resulting dipeptide modules may be connected to form tetrapeptide mimics. Specifically is described the mimicry of a four-residue segment of CD4, the cellular receptor of HIV-1. The design was based on molecular modeling and the X-ray crystal structures of CD4 and intended to present the most important-side chains and backbone elements of the Phe43-Lys46 segment.

  DOI：

  10.1021/jo9522771
• 作为产物：
  描述：

  [(S)-3-(1-Benzyl-4-oxo-piperidin-3-yl)-1-(2-tert-butoxycarbonylamino-ethylcarbamoyl)-3-oxo-propyl]-carbamic acid benzyl ester 在 palladium on activated charcoal 作用下， 以 甲醇 、 环己烯 为溶剂， 生成 {2-[((S)-6-Benzyl-4-oxo-1,2,3,4,5,6,7,8-octahydro-[1,6]naphthyridine-2-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design and Asymmetric Synthesis of β-Strand Peptidomimetics

  摘要：

  We describe the asymmetric synthesis of non-peptidic compounds that feature rigid backbone conformations and present various side-chain functions. The key step in the synthesis of these compounds is the C-acylation of an appropriate ketone with a suitably protected aspartic acid derivative. The resulting dipeptide modules may be connected to form tetrapeptide mimics. Specifically is described the mimicry of a four-residue segment of CD4, the cellular receptor of HIV-1. The design was based on molecular modeling and the X-ray crystal structures of CD4 and intended to present the most important-side chains and backbone elements of the Phe43-Lys46 segment.

  DOI：

  10.1021/jo9522771

文献信息

• Design and Asymmetric Synthesis of β-Strand Peptidomimetics
  作者：Ahcene Boumendjel、John C. Roberts、Essa Hu、Peter V. Pallai、Julius Rebek

  DOI：10.1021/jo9522771

  日期：1996.1.1

  We describe the asymmetric synthesis of non-peptidic compounds that feature rigid backbone conformations and present various side-chain functions. The key step in the synthesis of these compounds is the C-acylation of an appropriate ketone with a suitably protected aspartic acid derivative. The resulting dipeptide modules may be connected to form tetrapeptide mimics. Specifically is described the mimicry of a four-residue segment of CD4, the cellular receptor of HIV-1. The design was based on molecular modeling and the X-ray crystal structures of CD4 and intended to present the most important-side chains and backbone elements of the Phe43-Lys46 segment.