(3(2S),4S)-3-(5-azido-2-methyl-1-oxovaleryl)-4-benzyl-2-oxazolidinone | 868248-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (3(2S),4S)-3-(5-azido-2-methyl-1-oxovaleryl)-4-benzyl-2-oxazolidinone
• 英文别名: (2S)-1-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-5-azido-2-methyl-1-pentanone；(4S)-3-[(2S)-5-azido-2-methylpentanoyl]-4-benzyl-1,3-oxazolidin-2-one
• CAS: 868248-77-5
• 化学式: C₁₆H₂₀N₄O₃
• 分子量: 316.36
• InChiKey: LFWCAOGJUBKENT-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3(2S),4S)-3-(5-azido-2-methyl-1-oxovaleryl)-4-benzyl-2-oxazolidinone 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以96%的产率得到(2S)-5-叠氮基-2-甲基戊酸
  参考文献：
  名称：

  Synthesis of Cα methylated carboxylic acids: isosteres of arginine and lysine for use as N-terminal capping residues in polypeptides

  摘要：

  Replacement of the N-terminal alpha-amine with the isosteric methyl functionality in bioactive peptides can influence various pharmacokinetic parameters, including hydrophobicity and stability. C-alpha methylated amino acid analogues are thus of great interest to expand the repertoire of nonnatural synthons available as N-terminal 'capping' residues for peptide-based drug design. Several novel arginine and lysine analogues stereo selectively modified in the C-alpha position with a methyl group in place of the alpha-amine were prepared. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.056
• 作为产物：
  描述：

  5-叠氮基戊酸 在 三甲基乙酰氯 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.5h， 生成 (3(2S),4S)-3-(5-azido-2-methyl-1-oxovaleryl)-4-benzyl-2-oxazolidinone
  参考文献：
  名称：

  Synthesis of Cα methylated carboxylic acids: isosteres of arginine and lysine for use as N-terminal capping residues in polypeptides

  摘要：

  Replacement of the N-terminal alpha-amine with the isosteric methyl functionality in bioactive peptides can influence various pharmacokinetic parameters, including hydrophobicity and stability. C-alpha methylated amino acid analogues are thus of great interest to expand the repertoire of nonnatural synthons available as N-terminal 'capping' residues for peptide-based drug design. Several novel arginine and lysine analogues stereo selectively modified in the C-alpha position with a methyl group in place of the alpha-amine were prepared. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.056

文献信息

• Modulation of the Passive Permeability of Semipeptidic Macrocycles: N- and C-Methylations Fine-Tune Conformation and Properties
  作者：Christian Comeau、Benjamin Ries、Thomas Stadelmann、Jacob Tremblay、Sylvain Poulet、Ulrike Fröhlich、Jérôme Côté、Pierre-Luc Boudreault、Rabeb Mouna Derbali、Philippe Sarret、Michel Grandbois、Grégoire Leclair、Sereina Riniker、Éric Marsault

  DOI：10.1021/acs.jmedchem.0c02036

  日期：2021.5.13
• Synthesis of Cα methylated carboxylic acids: isosteres of arginine and lysine for use as N-terminal capping residues in polypeptides
  作者：Kevin S. Orwig、Thomas A. Dix

  DOI：10.1016/j.tetlet.2005.08.056

  日期：2005.10

  Replacement of the N-terminal alpha-amine with the isosteric methyl functionality in bioactive peptides can influence various pharmacokinetic parameters, including hydrophobicity and stability. C-alpha methylated amino acid analogues are thus of great interest to expand the repertoire of nonnatural synthons available as N-terminal 'capping' residues for peptide-based drug design. Several novel arginine and lysine analogues stereo selectively modified in the C-alpha position with a methyl group in place of the alpha-amine were prepared. (c) 2005 Elsevier Ltd. All rights reserved.