(5S,6E,8Z,11Z)-20-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-5-[tert-butyl(diphenyl)silyl]oxyicosa-6,8,11-trienoic acid | 298691-13-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: (5S,6E,8Z,11Z)-20-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-5-[tert-butyl(diphenyl)silyl]oxyicosa-6,8,11-trienoic acid
• CAS: 298691-13-1
• 化学式: C₄₆H₆₇N₃O₅SSi
• 分子量: 802.207
• InChiKey: NCUYMNWTCUGTKJ-WTSREVMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.82
• 重原子数：
  56
• 可旋转键数：
  27
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5S,6E,8Z,11Z)-20-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-5-[tert-butyl(diphenyl)silyl]oxyicosa-6,8,11-trienoic acid 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 80.0h， 以74%的产率得到(5S,6E,8Z,11Z)-20-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-5-hydroxyicosa-6,8,11-trienoic acid
  参考文献：
  名称：

  The design and synthesis of a 5-HETE affinity chromatography ligand for 5-hydroxyeicosanoid dehydrogenase

  摘要：

  The first total synthesis of an omega-amino 5-HETE derivative 27 has been accomplished by a new counterclockwise strategy, in which C-1 is constructed first and C-20 last. The omega-amino 5-HETE derivative was transformed to an affinity chromatography ligand, the biotinylated 5-HETE 30. This affinity chromatography ligand is aimed at purifying the 5-hydroxyeicosanoid dehydrogenase enzyme, which is responsible for the conversion of 5-HETE to 5-oxo-ETE, a potent eosinophil chemotactic factor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00971-0
• 作为产物：
  描述：

  methyl (5S,6E,8Z,11Z)-20-amino-5-[tert-butyl(diphenyl)silyl]oxyicosa-6,8,11-trienoate 在 sodium hydroxide 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (5S,6E,8Z,11Z)-20-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-5-[tert-butyl(diphenyl)silyl]oxyicosa-6,8,11-trienoic acid
  参考文献：
  名称：

  The design and synthesis of a 5-HETE affinity chromatography ligand for 5-hydroxyeicosanoid dehydrogenase

  摘要：

  The first total synthesis of an omega-amino 5-HETE derivative 27 has been accomplished by a new counterclockwise strategy, in which C-1 is constructed first and C-20 last. The omega-amino 5-HETE derivative was transformed to an affinity chromatography ligand, the biotinylated 5-HETE 30. This affinity chromatography ligand is aimed at purifying the 5-hydroxyeicosanoid dehydrogenase enzyme, which is responsible for the conversion of 5-HETE to 5-oxo-ETE, a potent eosinophil chemotactic factor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00971-0

文献信息

• The design and synthesis of a 5-HETE affinity chromatography ligand for 5-hydroxyeicosanoid dehydrogenase
  作者：Subhash P Khanapure、Goutam Saha、William S Powell、Joshua Rokach

  DOI：10.1016/s0040-4039(00)00971-0

  日期：2000.7

  The first total synthesis of an omega-amino 5-HETE derivative 27 has been accomplished by a new counterclockwise strategy, in which C-1 is constructed first and C-20 last. The omega-amino 5-HETE derivative was transformed to an affinity chromatography ligand, the biotinylated 5-HETE 30. This affinity chromatography ligand is aimed at purifying the 5-hydroxyeicosanoid dehydrogenase enzyme, which is responsible for the conversion of 5-HETE to 5-oxo-ETE, a potent eosinophil chemotactic factor. (C) 2000 Elsevier Science Ltd. All rights reserved.