benzyl (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[5-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanyl-1,3,4-oxadiazol-2-yl]propanoate | 1360470-95-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[5-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanyl-1,3,4-oxadiazol-2-yl]propanoate
• CAS: 1360470-95-6
• 化学式: C₃₁H₃₉N₃O₁₄S
• 分子量: 709.728
• InChiKey: YMFOCNGJEUPQPV-JCEAUZKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  49
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  243
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  在 N-甲基吗啉 作用下， 以 乙醇 为溶剂， 反应 1.03h， 生成 benzyl (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[5-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanyl-1,3,4-oxadiazol-2-yl]propanoate
  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