1-O-hexadecyl-2-O-benzyl-sn-glycero-3-phosphocholine | 91326-84-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: 1-O-hexadecyl-2-O-benzyl-sn-glycero-3-phosphocholine
• 英文别名: [(2R)-3-hexadecoxy-2-phenylmethoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 91326-84-0
• 化学式: C₃₁H₅₈NO₆P
• 分子量: 571.778
• InChiKey: PNZPQXOINXUKOZ-WJOKGBTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  39
• 可旋转键数：
  27
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-hexadecyl-2-O-benzyl-sn-glycero-3-phosphocholine 在 钯 氢气 作用下， 以 乙醇 为溶剂， 50.0 ℃ 、101.32 kPa 条件下， 反应 72.0h， 以95%的产率得到1-O-十六烷基-SN-甘油基-3-胆碱磷酸
  参考文献：
  名称：

  D-和L-酒石酸对血小板活化因子，其对映异构体及其类似物的对映选择性合成。

  摘要：

  乙酰甘油醚磷脂酰胆碱（血小板激活因子；PAFs）、其对映体及其类似物以立体化学明确的方式有效合成，起始于D-和L-酒石酸作为手性合成前体。C16-PAF的对映体（S-构型）显示出远低于天然PAF（R-构型）的活性，而N-甲基哌啶和N-甲基吡咯烷的类似物则显示出比天然C16-PAF更高的活性。

  DOI：

  10.1248/cpb.33.572
• 作为产物：
  描述：

  1-十六烷醇 在 三氟化硼乙醚 吡啶 、 lithium aluminium tetrahydride 、 2,6-二叔丁基-4-甲基吡啶 、 cesium acetate 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 生成 1-O-hexadecyl-2-O-benzyl-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  Novel enantioselective synthesis of platelet activating factor and its enantiomer via ring opening of glycidyl tosylate with 1-hexadecanol

  摘要：

  DOI：

  10.1016/s0040-4039(00)80503-1

文献信息

• Sphingolipids and Glycerolipids. Part III. Syntheses of a Glycerophospholipid, C16-Platelet Activating Factor and a Palmitoyl Analogue of M-5, an Anti-inflammatory Glyceroglycolipid.
  作者：Hirotaka SHIBUYA、Keiko KAWASHIMA、Norihiko NARITA、Isao KITAGAWA

  DOI：10.1248/cpb.40.1166

  日期：——

  From a chiral C4-epoxide (-)-3, which is one of the synthons in our synthetic strategy for complex lipids, a glycerophospholipid C16-platelet activating factor (C16-PAF, 1) and a palmitoyl analogue (2) of an anti-inflammatory glyceroglycolipid M-5, which was previously isolated from the Okinawan marine sponge Phyllospongia foliascens, have been synthesized.

  我们从手性 C4-环氧化物 (-)-3 中合成了一种甘油磷脂 C16-血小板活化因子（C16-PAF，1）和一种抗炎甘油糖脂 M-5 的棕榈酰类似物（2），前者是我们从冲绳海洋海绵 Phyllospongia foliascens 中分离出来的。
• New optically pure dimethylacetals of glyceraldehydes and their application for lipid and phospholipid synthesis
  作者：Ulrich Massing、Hansjörg Eibl

  DOI：10.1016/0009-3084(95)02445-o

  日期：1995.6

  A convenient synthesis of new and enantiomerically pure 2-O-protected D-glyceraldehyde dimethylacetals as chiral C-3 building blocks for the synthesis of lipids and phospholipids is described. Benzyl- or allylethers are used as protecting groups in position 2 and 5 of D-mannitol. These intermediates are converted to 2-O-benzyl- or 2-O-allyl-D-glyceraldehyde dimethylacetals by cleavage with periodic acid in methanol. The two dimethylacetals are useful for the synthesis of mixed chain phospholipids with natural configuration of ester-ester, ester-ether or ether-ether composition. Also, triglycerides with three different alkyl chains, ester or ether, can be prepared. As an example of the versatility of the new intermediates, we describe the synthesis of 1-O-hexahecyl-2-O-acetyl-sn-glycero-3-phosphocholine, the so-called 'platelet activating factor' (PAF), via 1-O-hexadecyl-2-O-benzyl-sn-glycerol.
• An efficient stereocontrolled route to both enantiomers of platelet activating factor and analogs with long-chain esters at C-2: saturated and unsaturated ether glycerolipids by opening of glycidyl arenesulfonates
  作者：Pedro N. Guivisdalsky、Robert Bittman

  DOI：10.1021/jo00280a035

  日期：1989.9
• Synthesis and Biological Activity of Anticancer Ether Lipids That Are Specifically Released by Phospholipase A₂ in Tumor Tissue
  作者：Thomas L. Andresen、Simon S. Jensen、Robert Madsen、Kent Jørgensen

  DOI：10.1021/jm049006f

  日期：2005.11.1

  The clinical use of anticancer lipids is severely limited by their ability to cause lysis of red blood cells prohibiting intravenous injection. Novel delivery systems are therefore required in order to develop anticancer ether lipids (AELs) into clinically useful anticancer drugs. In a recent article (J. Med. Chem. 2004, 4 7, 1694) we showed that it is possible to construct liposome systems composed of masked AELs that are activated by secretory phospholipase A(2) in cancerous tissue. We present here the synthesis of six AELs and evaluate the biological activity of these bioactive lipids. The synthesized AEL 1-6 were tested against three different cancer cell lines. It was found that the stereochemistry of the glycerol headgroup in AEL-2 and 3 has a dramatic effect on the cytotoxicity of the lipids. AEL 1-4 were furthermore evaluated for their ability to prevent phosphorylation of the apoptosis regulating kinase Akt, and a correlation was found between their cytotoxic activity and their ability to inhibit Akt phosphorylation.
• Trimethylsilyl triflate mediated introduction of phospholipid head groups
  作者：Thomas R. Gadek

  DOI：10.1016/s0040-4039(00)95277-8

  日期：1989.1