(S)-methyl 2-(3-(N-tert-butoxycarbonyl)thioureido)-3-phenylpropanoate | 1542155-98-5

• 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: (S)-methyl 2-(3-(N-tert-butoxycarbonyl)thioureido)-3-phenylpropanoate
• CAS: 1542155-98-5
• 化学式: C₁₆H₂₂N₂O₄S
• 分子量: 338.428
• InChiKey: YMKDSZASZYWGQO-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  76.66
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 、 N,N′-二-Boc-硫脲 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.25h， 以11%的产率得到(S)-methyl 2-(3-(N-tert-butoxycarbonyl)thioureido)-3-phenylpropanoate
  参考文献：
  名称：

  Solid-Phase Synthesis of Peptide Thioureas and Thiazole-Containing Macrocycles through Ru-Catalyzed Ring-Closing Metathesis

  摘要：

  N-Terminally modified alpha-thiourea peptides can selectively be synthesized on solid support under mild reaction conditions using N,N'-di-Boc-thiourea and Mukaiyama's reagent (2-chloro-l-methyl-pyridinium iodide). This N-terminal modification applies to the 20 proteinogenic amino acid residues on three commonly used resins for solid-phase synthesis. Complementary methods for the synthesis of alpha-guanidino peptides have also been developed. The thiourea products underwent quantitative reactions with alpha-halo ketones to form thiazoles in excellent purities and yields. When strategically installed between two alkene moieties, said thiazole core was conveniently embedded in peptide macrocycles via Ru-catalyzed ring-closing metathesis reactions. Various 15-17 membered macrocycles were easily accessible in all diastereomeric forms using this methodology. The developed "build/couple/pair" strategy is well suited for the generation of larger and stereochemically complete screening libraries of thiazole-containing peptide macrocycles.

  DOI：

  10.1021/co400102v