methyl (S)-2-bromo-4-(methylthio)butanoate | 1360470-97-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (S)-2-bromo-4-(methylthio)butanoate
• CAS: 1360470-97-8
• 化学式: C₆H₁₁BrO₂S
• 分子量: 227.122
• InChiKey: VXVPYBZDTCXYFZ-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  10.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-bromo-4-(methylthio)butanoate 、 tert-butyl (S)-((5-mercapto-1,3,4-oxadiazol-2-yl)(phenyl)methyl)carbamate 在 N-甲基吗啉 作用下， 以 乙醇 为溶剂， 反应 0.63h， 以81%的产率得到methyl (R)-2-((5-((S)-((tert-butoxycarbonyl)amino)(phenyl)methyl)-1,3,4-oxadiazol-2-yl)thio)-4-(methylthio)butanoate
  参考文献：
  名称：

  A facile one-pot synthesis of Nα-Z/Boc-protected S-linked 1,3,4-oxadiazole tethered peptidomimetics

  摘要：

  A new class of S-linked 1,3,4-oxadiazole-tethered N-alpha-protected peptidomimetics is designed and synthesized by a reaction of N-alpha-Z/Boc-protected 1,3,4-oxadiazole-2-thiol with alpha-bromo ester derived from amino acid. The protocol has also been employed for the synthesis of glycosylated amino acids and N,N'-orthogonally protected dipeptidomimetics bearing S-linked 1,3,4-oxadiazole mimetics as well. The intermediate 5-alkyl amino-1,3,4-oxadiazole-2-thiols have been isolated as stable compounds. Further, the chain extension at both N- and C-termini of N-protected S-linked 1,3,4-oxadiazole tethered dipeptidomimetics was also demonstrated. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.093