Hexadecanoic acid (R)-3-[(2-tert-butoxycarbonylamino-ethoxy)-hydroxy-phosphoryloxy]-2-{(Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoyloxy}-propyl ester | 878754-16-6

• 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: Hexadecanoic acid (R)-3-[(2-tert-butoxycarbonylamino-ethoxy)-hydroxy-phosphoryloxy]-2-{(Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoyloxy}-propyl ester
• 英文别名: [(2R)-2-[(Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoyl]oxy-3-[hydroxy-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]phosphoryl]oxypropyl] hexadecanoate
• CAS: 878754-16-6
• 化学式: C₄₆H₈₄NO₁₃P
• 分子量: 890.146
• InChiKey: ZSYGRVAOYVFXEJ-JFFHRZTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  61
• 可旋转键数：
  40
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  207
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Hexadecanoic acid (R)-3-[(2-tert-butoxycarbonylamino-ethoxy)-hydroxy-phosphoryloxy]-2-{(Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoyloxy}-propyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以0.2 mg的产率得到Hexadecanoic acid (R)-3-[(2-amino-ethoxy)-hydroxy-phosphoryloxy]-2-{(Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoyloxy}-propyl ester
  参考文献：
  名称：

  Synthesis of Isoprostanyl Phosphatidylcholine and Isoprostanyl Phosphatidylethanolamine

  摘要：

  The syntheses of two isoprostanyl phospholipids are described. A newly established route to 15-F-2t-isoprostane and ent-15-epi-F-2t-isoprostane has allowed for the selective preparation of 15-F-2t-isoprostanyl phosphatidylethanolamine and ent-15-epi-F-2t-isoprostanyl phosphatidylcholine. The nature of the head-groups dictates the coupling strategy used to attach the appropriately protected isoprostanes to the corresponding lysophospholipids. Preliminary H-1 NMR and P-31 NMR studies indicate that these isoprostanyl phospholipids aggregate in apolar solvents.

  DOI：

  10.1021/jo0518553
• 作为产物：
  描述：

  (Z)-7-[(1S,2R,3R,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]cyclopentyl]hept-5-enoic acid 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丁酮 为溶剂， 反应 82.5h， 生成 Hexadecanoic acid (R)-3-[(2-tert-butoxycarbonylamino-ethoxy)-hydroxy-phosphoryloxy]-2-{(Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoyloxy}-propyl ester
  参考文献：
  名称：

  Synthesis of Isoprostanyl Phosphatidylcholine and Isoprostanyl Phosphatidylethanolamine

  摘要：

  The syntheses of two isoprostanyl phospholipids are described. A newly established route to 15-F-2t-isoprostane and ent-15-epi-F-2t-isoprostane has allowed for the selective preparation of 15-F-2t-isoprostanyl phosphatidylethanolamine and ent-15-epi-F-2t-isoprostanyl phosphatidylcholine. The nature of the head-groups dictates the coupling strategy used to attach the appropriately protected isoprostanes to the corresponding lysophospholipids. Preliminary H-1 NMR and P-31 NMR studies indicate that these isoprostanyl phospholipids aggregate in apolar solvents.

  DOI：

  10.1021/jo0518553