tert-butyl (S)-2-((S)-6-(methoxycarbonyl)-12-oxo-14-phenyl-4-thioxo-13-oxa-2,3,5,11-tetraazatetradecanoyl)pyrrolidine-1-carboxylate | 1246168-75-1

• 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: tert-butyl (S)-2-((S)-6-(methoxycarbonyl)-12-oxo-14-phenyl-4-thioxo-13-oxa-2,3,5,11-tetraazatetradecanoyl)pyrrolidine-1-carboxylate
• CAS: 1246168-75-1
• 化学式: C₂₆H₃₉N₅O₇S
• 分子量: 565.691
• InChiKey: IUIZBTAOKZVSEV-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  147.33
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2-((S)-6-(methoxycarbonyl)-12-oxo-14-phenyl-4-thioxo-13-oxa-2,3,5,11-tetraazatetradecanoyl)pyrrolidine-1-carboxylate 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73%的产率得到tert-butyl (2S)-2-[5-[[(2S)-1-methoxy-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]amino]-1,3,4-oxadiazol-2-yl]pyrrolidine-1-carboxylate
  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
• 作为产物：
  描述：

  methyl (S)-6-(((benzyloxy)carbonyl)amino)-2-isothiocyanatohexanoate 、 2-(肼羰基)吡咯烷-1-羧酸-(S)-叔丁酯 以 四氢呋喃 为溶剂， 反应 1.0h， 以64%的产率得到tert-butyl (S)-2-((S)-6-(methoxycarbonyl)-12-oxo-14-phenyl-4-thioxo-13-oxa-2,3,5,11-tetraazatetradecanoyl)pyrrolidine-1-carboxylate
  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