methyl 2-[[(2S)-3-(1-formylindol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-[2-(phenylmethoxycarbonylamino)ethyl]amino]acetate | 143192-38-5

• 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: methyl 2-[[(2S)-3-(1-formylindol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-[2-(phenylmethoxycarbonylamino)ethyl]amino]acetate
• CAS: 143192-38-5
• 化学式: C₃₀H₃₆N₄O₈
• 分子量: 580.638
• InChiKey: ADZLBMHPPMJOKH-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  145
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-[Phenylmethoxycarbonyl-[2-(phenylmethoxycarbonylamino)ethyl]amino]acetic acid 在 盐酸 、 氯化亚砜 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 N,N-二异丙基乙胺 作用下， 反应 4.83h， 生成 methyl 2-[[(2S)-3-(1-formylindol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-[2-(phenylmethoxycarbonylamino)ethyl]amino]acetate
  参考文献：
  名称：

  Building units for N-backbone cyclic peptides. 1. Synthesis of protected N-(.omega.-aminoalkylene)amino acids and their incorporation into dipeptide units

  摘要：

  A variety of new amino acids which contain an omega-aminoalkylene group on the N(alpha)-amino nitrogen were synthesized by alkylation of alkylenediamines with alpha-halogeno acids. The reaction proceeds with inversion of configuration; thus, optically pure products were obtained when optically active a-halogeno acids were used. The N-(omega-aminoalkylene)amino acids were protected by orthogonal protecting groups to allow their incorporation into dipeptides by the "solution" techniques and into peptides by the solid-phase peptide synthesis (SPPS) methodology. A series of dipeptide analogs of Phe-Gly, Leu-Gly, Trp-Gly, Phe-Leu, and Phe-Ala in which the nitrogen of the peptide bond is alkylated by omega-aminoalkylene chains with various lengths were prepared. These new protected N-(omega-aminoalkylene)amino acids and their derived dipeptide units may be used as building blocks for conformationally constrained N-backbone cyclic peptides.

  DOI：

  10.1021/jo00047a022