methyl 5(S)-(tert-butyldiphenylsilyl)oxy-6-oxo-hexanoate | 298691-03-9

• 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 5(S)-(tert-butyldiphenylsilyl)oxy-6-oxo-hexanoate
• 英文别名: methyl (5S)-5-[tert-butyl(diphenyl)silyl]oxy-6-oxohexanoate
• CAS: 298691-03-9
• 化学式: C₂₃H₃₀O₄Si
• 分子量: 398.574
• InChiKey: ORIQEAACSPQYCK-IBGZPJMESA-N

物化性质

• 沸点：
  442.9±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5(S)-(tert-butyldiphenylsilyl)oxy-6-oxo-hexanoate 在 咪唑 、 sodium azide 、 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 、 苯 为溶剂， 反应 35.5h， 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
• 作为产物：
  描述：

  2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose 在 palladium on carbon 、 氢气 、 高碘酸 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 生成 methyl 5(S)-(tert-butyldiphenylsilyl)oxy-6-oxo-hexanoate
  参考文献：
  名称：

  C20-trifluoro-5-oxo-ETE: A metabolically stable 5-oxo-ETE derivative

  摘要：

  The total synthesis of C-20-trifluoro-6(E),8(Z),11(Z),14(Z) 5-oxo-ETE is reported. This compound was designed as an x-oxidation-resistant analog of 5-oxo-ETE that would be resistant to metabolism. The trifluoro derivative of 5-oxo-ETE stimulated calcium mobilization in neutrophils and desensitized these cells to subsequent exposure to 5-oxo-ETE. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.021

文献信息

• Design and synthesis of affinity chromatography ligands for the purification of 5-hydroxyeicosanoid dehydrogenase
  作者：Chintam Nagendra Reddy、Qiuji Ye、Pranav Patel、Sashikala Sivendran、Shishir Chourey、Rui Wang、Jaganmohan R. Anumolu、Gail E. Grant、William S. Powell、Joshua Rokach

  DOI：10.1016/j.bmc.2016.10.017

  日期：2017.1

  Our main goal is to determine how the biosynthesis of 5-oxo-ETE is regulated and to determine its pathophysiological roles. To achieve this task, we designed and synthesized affinity chromatography ligands for the purification of 5-hydroxyeicosanoid dehydrogenase (5-HEDH), the enzyme responsible for the formation of 5-oxo-ETE.

  花生四烯酸（AA）通过不同的途径转化为具有生物活性的代谢物，其中最重要的途径之一是由5-脂氧合酶（5-LO）引发的。5-羟基己二酸四氢呋喃酸（5-HETE）本身仅具有较弱的生物活性，但会被氧化为5-氧代-6,8,11,14-二十碳四烯酸（5-oxo-ETE），对嗜酸性粒细胞和嗜中性粒细胞有很强的化学吸引力。 。我们的主要目标是确定如何调节5-oxo-ETE的生物合成并确定其病理生理作用。为实现此任务，我们设计并合成了亲和色谱配体，用于纯化5-羟基二十烷酸脱氢酶（5-HEDH），该酶负责形成5-oxo-ETE。
• Total Synthesis of 8,12-<i>iso</i>-iPF₃_α-VI, an EPA-Derived Isoprostane:  Stereoselective Introduction of the Fifth Asymmetric Center
  作者：Sheila H. Jacobo、Chih-Tsung Chang、Gue-Jae Lee、John A. Lawson、William S. Powell、Domenico Pratico、Garret A. FitzGerald、Joshua Rokach

  DOI：10.1021/jo051916x

  日期：2006.2.1

  A new and stereoselective approach for the synthesis of all-syn isoprostanes is reported. This method, which is based on acid-catalyzed Diels-Alder reaction, allows the introduction of the side chain with a predetermined stereochemistry of the hydroxy group. The first total synthesis of an eicosapentaenoic acid (EPA)-derived iP, 8,12-iso-iPF(3 alpha)-VI 10, was performed using this approach.
• 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.
• C20-trifluoro-5-oxo-ETE: A metabolically stable 5-oxo-ETE derivative
  作者：Pranav Patel、Vivek Gore、William S. Powell、Joshua Rokach

  DOI：10.1016/j.bmcl.2011.02.021

  日期：2011.4

  The total synthesis of C-20-trifluoro-6(E),8(Z),11(Z),14(Z) 5-oxo-ETE is reported. This compound was designed as an x-oxidation-resistant analog of 5-oxo-ETE that would be resistant to metabolism. The trifluoro derivative of 5-oxo-ETE stimulated calcium mobilization in neutrophils and desensitized these cells to subsequent exposure to 5-oxo-ETE. (C) 2011 Elsevier Ltd. All rights reserved.