[(2R)-3-十六烷氧基-2-甲氧基丙基] 2-三甲基铵乙基磷酸酯 | 78858-44-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 中文名称: [(2R)-3-十六烷氧基-2-甲氧基丙基] 2-三甲基铵乙基磷酸酯
• 中文别名: [(2R)-3-十六烷氧基-2-甲氧基丙基]2-三甲基铵乙基磷酸酯
• 英文名称: 1-O-hexadecyl-2-O-methyl-sn-glycero(3)phosphocholine
• 英文别名: 1-O-hexadecyl-2-O-methyl-sn-glycero-3-phosphocholine；3-O-hexadecyl-2-O-methyl-sn-glycero-1-phosphocholine；1-hexadecyl-2-methyl-sn-glycero-3-phosphocholine；1-O-hexadecyl-2-O-methyl-sn-3-glycerophosphocholine；(2r)-3-(Hexadecyloxy)-2-methoxypropyl 2-(trimethylammonio)ethyl phosphate；[(2R)-3-hexadecoxy-2-methoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 78858-44-3
• 化学式: C₂₅H₅₄NO₆P
• mdl: MFCD00065892
• 分子量: 495.681
• InChiKey: RZNRKXGAJMGLIM-RUZDIDTESA-N

物化性质

• 溶解度：
  PBS（pH 7.2）：5 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  33
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-十六烷醇 在 18-冠醚-6 potassium superoxide 、 2,6-二叔丁基-4-甲基吡啶 、 三氟化硼乙醚 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 氯仿 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 84.0h， 生成 [(2R)-3-十六烷氧基-2-甲氧基丙基] 2-三甲基铵乙基磷酸酯
  参考文献：
  名称：

  Regiospecific opening of glycidyl derivatives mediated by boron trifluoride. Asymmetric synthesis of ether-linked phospholipids

  摘要：

  DOI：

  10.1021/jo00280a034

文献信息

• A new approach to the synthesis of ether phospholipids. Preparation of 1,2-dialkylglycerophosphorylcholines from L-glyceric acid
  作者：Suresh K Bhatia、Joseph Hajdu

  DOI：10.1016/s0040-4039(00)95704-6

  日期：1987.1

  A novel stereospecific synthesis of antitumor active ether phospholipids is reported.

  报道了抗肿瘤活性醚磷脂的新型立体有择合成。
• An enantioselective synthesis of platelet-activating factors, their enantiomers, and their analogues from D- and L-tartaric acids.
  作者：MASAJI OHNO、KAGARI FUJITA、HISAO NAKAI、SUSUMU KOBAYASHI、KEIZO INOUE、SHOSHICHI NOJIMA

  DOI：10.1248/cpb.33.572

  日期：——

  Acetyl glyceryl ether phosphorylcholines (platelet-activating factors ; PAFs), their enantiomers, and their analogues were efficiently synthesized in a stereochemically unambiguous manner starting from D-and L-tartaric acids as chiral synthons. The enantiomer of C16-PAF (S-comfiguration) showed far less activity than the natural PAF (R-configuration), and the N-methylpiperidine and N-methylpyrrolidine analogues were found to possess much higher activity than natural C16-PAF.

  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。
• Stereospecific synthesis of ether and thioether phospholipids. The use of L-glyceric acid as a chiral phospholipid precursor
  作者：Suresh K. Bhatia、Joseph Hajdu

  DOI：10.1021/jo00256a024

  日期：1988.10
• Antitumor phospholipids: A one-pot introduction of a phosphocholine moiety into lipid hydroxy acceptors
  作者：Ravi Kumar Erukulla、Hoe-Sup Byun、Robert Bittman

  DOI：10.1016/s0040-4039(00)78183-4

  日期：1994.8
• METHOD OF ENHANCING TRANSMUCOSAL DELIVERY OF THERAPEUTIC COMPOUNDS
  申请人：Quay C. Steven

  公开号：US20070077283A1

  公开（公告）日：2007-04-05

  A composition comprising a biologically active agent and a permeation enhancing lipid wherein the permeation enhancing lipid is a platelet activating factor antagonist or a biologically inactive a platelet activating factor, and increases permeability of the biologically active agent across a tissue layer. Also disclosed is a process of increasing the permeability of a biological agent across a layer tissue comprising contacting the tissue layer with a composition comprising the biological agent and a permeation enhancing lipid wherein the permeation enhancing lipid is a platelet activating factor antagonist or a biologically inactive platelet activating factor.