(S)-methyl-2-((5-((S)-1-(((benzyloxy)carbonyl)amino)-2-phenylethyl)-1,3,4-oxadiazol-2-yl)amino)propanoate | 1246168-67-1

• 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-((5-((S)-1-(((benzyloxy)carbonyl)amino)-2-phenylethyl)-1,3,4-oxadiazol-2-yl)amino)propanoate
• 英文别名: Z-Phe-ψ-[C2N2O]-L-Ala-OMe；methyl (2S)-2-[[5-[(1S)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]-1,3,4-oxadiazol-2-yl]amino]propanoate
• CAS: 1246168-67-1
• 化学式: C₂₂H₂₄N₄O₅
• 分子量: 424.456
• InChiKey: LYSSKGDZIJMERA-YJBOKZPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  Z-Phe-ψ-[CONHNHCSNH]-L-Ala-OMe 在 吡啶 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以84%的产率得到(S)-methyl-2-((5-((S)-1-(((benzyloxy)carbonyl)amino)-2-phenylethyl)-1,3,4-oxadiazol-2-yl)amino)propanoate
  参考文献：
  名称：

  A facile synthesis of N-Z/Boc-protected 1,3,4-oxadiazole-based peptidomimetics employing peptidyl thiosemicarbazides

  摘要：

  Synthesis of 1,3,4-oxadiazole containing peptidomimetics is described by a p-TsCl/pyridine-mediated cyclization of the corresponding dipeptidyl thiosemicarbazides, which are readily prepared by coupling N-protected amino acid hydrazides with amino acid-derived isothiocyanato esters. Further, the protocol has also been extended for the synthesis of orthogonally protected 1,3,4-oxadiazole tethered mimetics as well. The synthetic route is simple and mild conditions are used so that the chirality of the starting amino acids is retained. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.004

文献信息

• Facile one-pot synthesis of 2-amino-1,3,4-oxadiazole tethered peptidomimetics by molecular-iodine-mediated cyclodeselenization
  作者：L. Santhosh、C. Srinivasulu、S. Durgamma、Girish Prabhu、Vommina V. Sureshbabu

  DOI：10.1039/c7nj02278f

  日期：——

  Synthesis of 2-amino-1,3,4-oxadiazole tethered peptidomimetics through the reaction of Nα-protected amino acid hydrazides with isoselenocyanato esters in one- pot is described. The molecular-iodine-mediated cyclodeselenization of in situ generated selenosemicarbazide intermediates resulted in the facile formation of 2-amino-1,3,4-oxadiazoles under mild conditions in excellent yields. The method employs

  描述了通过一锅中Nα-保护的氨基酸酰肼与异戊烯基氰基酸酯的反应合成2-氨基-1,3,4-恶二唑束缚的拟肽。分子碘介导的原位生成的硒代氨基脲化合物中间体的环二硒化导致在温和条件下以优异的产率容易地形成2-氨基-1,3,4-恶二唑。该方法采用对环境无害的碘作为环化剂，从而避免了现有路线中所采用的苛刻条件。
• A facile synthesis of N-Z/Boc-protected 1,3,4-oxadiazole-based peptidomimetics employing peptidyl thiosemicarbazides
  作者：Ravi S. Lamani、G. Nagendra、Vommina V. Sureshbabu

  DOI：10.1016/j.tetlet.2010.07.004

  日期：2010.9

  Synthesis of 1,3,4-oxadiazole containing peptidomimetics is described by a p-TsCl/pyridine-mediated cyclization of the corresponding dipeptidyl thiosemicarbazides, which are readily prepared by coupling N-protected amino acid hydrazides with amino acid-derived isothiocyanato esters. Further, the protocol has also been extended for the synthesis of orthogonally protected 1,3,4-oxadiazole tethered mimetics as well. The synthetic route is simple and mild conditions are used so that the chirality of the starting amino acids is retained. (C) 2010 Elsevier Ltd. All rights reserved.