[(2R)-2-[(Z)-7-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]cyclopentyl]hept-5-enoyl]oxy-3-[2-chloroethoxy(methoxy)phosphoryl]oxypropyl] hexadecanoate | 878754-19-9

• 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: [(2R)-2-[(Z)-7-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]cyclopentyl]hept-5-enoyl]oxy-3-[2-chloroethoxy(methoxy)phosphoryl]oxypropyl] hexadecanoate
• CAS: 878754-19-9
• 化学式: C₆₀H₁₁₈ClO₁₁PSi₃
• 分子量: 1166.27
• InChiKey: XWBSLRJKZCHSGW-GZJZDSPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.01
• 重原子数：
  76
• 可旋转键数：
  47
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2R)-2-[(Z)-7-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]cyclopentyl]hept-5-enoyl]oxy-3-[2-chloroethoxy(methoxy)phosphoryl]oxypropyl] hexadecanoate 在 盐酸 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 水 为溶剂， 反应 70.0h， 生成 [(2R)-2-[(Z)-7-[(1R,2S,3S,5R)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoyl]oxy-3-hexadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
  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：

  1-palmitoyl-3-(4-methoxybenzyl)-sn-glycerol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 水 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 23.0 ℃ 、101.33 kPa 条件下， 反应 29.0h， 生成 [(2R)-2-[(Z)-7-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]cyclopentyl]hept-5-enoyl]oxy-3-[2-chloroethoxy(methoxy)phosphoryl]oxypropyl] hexadecanoate
  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

文献信息

• Synthesis of Isoprostanyl Phosphatidylcholine and Isoprostanyl Phosphatidylethanolamine
  作者：Manami Shizuka、Thomas O. Schrader、Marc L. Snapper

  DOI：10.1021/jo0518553

  日期：2006.2.1

  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.