methyl (5S,6E,8Z,11Z)-20-amino-5-[tert-butyl(diphenyl)silyl]oxyicosa-6,8,11-trienoate | 298691-11-9

• 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 (5S,6E,8Z,11Z)-20-amino-5-[tert-butyl(diphenyl)silyl]oxyicosa-6,8,11-trienoate
• CAS: 298691-11-9
• 化学式: C₃₇H₅₅NO₃Si
• 分子量: 589.934
• InChiKey: HGXODZHWLYCOLF-NSQGWSOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.02
• 重原子数：
  42
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.0h， 生成 (5S,6E,8Z,11Z)-20-[(2-azido-5-iodobenzoyl)amino]-5-[tert-butyl(diphenyl)silyl]oxyicosa-6,8,11-trienoic acid
  参考文献：
  名称：

  The synthesis of a 5-HETE photoaffinity ligand

  摘要：

  The design and synthesis of a photoaffinity ligand 26, targeted at the 5h-dh, was accomplished. The synthesis was effected by two new synthetic routes which focus on the omega-hydroxy 5-HETE derivative 12 as a pivotal synthon. Preliminary results show ligand 26 to be an excellent substrate for the 5h-dh. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01064-9
• 作为产物：
  描述：

  2-(9-溴壬基-1-氧基)四氢吡喃 在 咪唑 、 sodium azide 、 四丁基氟化铵 、 碘 、 二甲基氯化铝 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 147.5h， 生成 methyl (5S,6E,8Z,11Z)-20-amino-5-[tert-butyl(diphenyl)silyl]oxyicosa-6,8,11-trienoate
  参考文献：
  名称：

  The synthesis of a 5-HETE photoaffinity ligand

  摘要：

  The design and synthesis of a photoaffinity ligand 26, targeted at the 5h-dh, was accomplished. The synthesis was effected by two new synthetic routes which focus on the omega-hydroxy 5-HETE derivative 12 as a pivotal synthon. Preliminary results show ligand 26 to be an excellent substrate for the 5h-dh. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01064-9

文献信息

• A photoaffinity probe for 5-hydroxyeicosanoid dehydrogenase suitable for radioiodination
  作者：Seongjin Kim、Yurdanur Adiyaman、Goutam Saha、William S Powell、Joshua Rokach

  DOI：10.1016/s0040-4039(01)00699-2

  日期：2001.7

  5-Hydroxy eicosanoid dehydrogenase (5h-dh) is a key enzyme responsible for the biosynthesis of 5-oxo-ETE, a potent eosinophil chemoattractant. To facilitate the identification and characterization of jh-dh we have synthesized a photoaffinity ligand 7, designed to bind to the enzyme, and shown it to be an excellent substrate for Sh-dh. We have also synthesized a precursor 34, containing the photoaffinity label and a trimethyl tin group that can readily be displaced by iodide and will be suitable for radioiodination with I-125. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.
• The synthesis of a 5-HETE photoaffinity ligand
  作者：Goutam Saha、Subhash P Khanapure、William S Powell、Joshua Rokach

  DOI：10.1016/s0040-4039(00)01064-9

  日期：2000.8

  The design and synthesis of a photoaffinity ligand 26, targeted at the 5h-dh, was accomplished. The synthesis was effected by two new synthetic routes which focus on the omega-hydroxy 5-HETE derivative 12 as a pivotal synthon. Preliminary results show ligand 26 to be an excellent substrate for the 5h-dh. (C) 2000 Elsevier Science Ltd. All rights reserved.