(R)-1-O-hexadecyl-2-O-benzyl-3-(p-toluenesulfonyl)glycerol | 121469-38-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1-O-hexadecyl-2-O-benzyl-3-(p-toluenesulfonyl)glycerol
• 英文别名: 1-O-hexadecyl-2-O-benzyl-sn-glycerol 3-O-p-toluenesulfonate；(R)-2-(benzyloxy)-3-(hexadecyloxy)propyl 4-methylbenzene sulfonate；[(2R)-3-hexadecoxy-2-phenylmethoxypropyl] 4-methylbenzenesulfonate
• CAS: 121469-38-3
• 化学式: C₃₃H₅₂O₅S
• 分子量: 560.839
• InChiKey: ANKJFTOMXXDQKM-JGCGQSQUSA-N

物化性质

• 沸点：
  646.3±55.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  39
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-1-O-hexadecyl-2-O-benzyl-3-(p-toluenesulfonyl)glycerol 在 palladium dihydroxide 吡啶 、 lithium aluminium tetrahydride 、 氢气 、 cesium acetate 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 2-hydroxy-3-(hexadecyloxy)-propyl 2-trimethylammonioethyl phosphate
  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
• 作为产物：
  描述：

  1-十六烷醇 在 三氟甲磺酸 、 三氟化硼乙醚 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 39.0h， 生成 (R)-1-O-hexadecyl-2-O-benzyl-3-(p-toluenesulfonyl)glycerol
  参考文献：
  名称：

  [EN] PHOSPHOLIPID COMPOUNDS AND USES THEREOF
  [FR] COMPOSÉS PHOSPHOLIPIDIQUES ET LEURS UTILISATIONS

  摘要：

  本文披露了化合物及使用该化合物的方法，可单独使用或与其他药剂联合使用，并且该化合物的制药组合物用于治疗病毒感染（式子（I））。

  公开号：

  WO2022046631A1

文献信息

• 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.
• GUIVISCLALSKY, PEDRO N.;BITTMAN, ROBERT, TETRAHEDRON LETT., 29,(1988) N 35, C. 4393-4396
  作者：GUIVISCLALSKY, PEDRO N.、BITTMAN, ROBERT

  DOI：——

  日期：——
• Novel enantioselective synthesis of platelet activating factor and its enantiomer via ring opening of glycidyl tosylate with 1-hexadecanol
  作者：Pedro N. Guivisdalsky、Robert Bittman

  DOI：10.1016/s0040-4039(00)80503-1

  日期：1988.1
• [EN] PHOSPHOLIPID COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS PHOSPHOLIPIDIQUES ET LEURS UTILISATIONS
  申请人：GILEAD SCIENCES INC

  公开号：WO2022046631A1

  公开（公告）日：2022-03-03

  Compounds and methods of using said compounds, singly or in combination with additional agents, and pharmaceutical compositions of said compounds for the treatment of viral infections are disclosed (Formula (I)).

  本文披露了化合物及使用该化合物的方法，可单独使用或与其他药剂联合使用，并且该化合物的制药组合物用于治疗病毒感染（式子（I））。