(4S)-3-[(2S)-6-bromo-2-methylhexanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one | 862828-08-8

• 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: (4S)-3-[(2S)-6-bromo-2-methylhexanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one
• 英文别名: (3(2S),4S)-3-(2-methyl-6-bromo-1-oxohexyl)-4-(phenylmethyl)-2-oxazolidinone；(3(2S),4S)-3-(2-methyl-6-bromo-1-oxohexanyl)-4-(phenylmethyl)-2-oxazolidinone；(4S)-4-benzyl-3-[(2S)-6-bromo-2-methylhexanoyl]-1,3-oxazolidin-2-one
• CAS: 862828-08-8
• 化学式: C₁₇H₂₂BrNO₃
• 分子量: 368.271
• InChiKey: VPLGNIUYISAOKX-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-3-[(2S)-6-bromo-2-methylhexanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以89%的产率得到6-叠氮基己酸
  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：

  (S)-4-benzyl-3-(6-bromo-1-oxohexyl)-2-oxazolidinone 、 碘甲烷 在 双(三甲基硅烷基)氨基钾 、 溶剂黄146 作用下， 反应 1.0h， 以10%的产率得到(4S)-3-[(2S)-6-bromo-2-methylhexanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  [EN] NON-NATURAL AMINO ACIDS
  [FR] ACIDES AMINES NON NATURELS

  摘要：

  公开号：

  WO2006009902A3

文献信息

• Asymmetric Synthesis of ω‐Bromo‐2(S)‐Methyl Acids as Precursors for Novel Arginine, Lysine, and Mercapto Residues
  作者：M. Kyle Hadden、Kyle P. Kokko、Thomas A. Dix

  DOI：10.1081/scc-200061668

  日期：2005.6.1

  Abstract A series of ω‐bromo‐2(S)‐methyl acids has been synthesized as precursors of novel arginine (Arg), lysine (Lys), and mercapto analogues. These intermediates contain α‐methyl groups and are designed to mask the N‐terminal amine when incorporated in pharmaceutically relevant peptides.

  摘要 已经合成了一系列 ω-溴-2(S)-甲基酸作为新型精氨酸 (Arg)、赖氨酸 (Lys) 和巯基类似物的前体。这些中间体含有 α-甲基，当掺入药物相关的肽中时，它们旨在掩盖 N 端胺。
• [EN] NON-NATURAL AMINO ACIDS<br/>[FR] ACIDES AMINES NON NATURELS
  申请人：UNIV SOUTH CAROLINA

  公开号：WO2006009902A3

  公开（公告）日：2006-12-28
• 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.
• WO2007/70672
  申请人：——

  公开号：——

  公开（公告）日：——