4-(1-thio-β-D-glucopyranosido)-2,3,5,6-tetrafluorostyrene | 1268156-62-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(1-thio-β-D-glucopyranosido)-2,3,5,6-tetrafluorostyrene
• CAS: 1268156-62-2
• 化学式: C₁₄H₁₄F₄O₅S
• 分子量: 370.322
• InChiKey: AVTXUCJKGYRDSK-QPUPYUFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  90.15
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4-(2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosido)-2,3,5,6-tetrafluorostyrene 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以93%的产率得到4-(1-thio-β-D-glucopyranosido)-2,3,5,6-tetrafluorostyrene
  参考文献：
  名称：

  Functionalized, Biocompatible Coating for Superparamagnetic Nanoparticles by Controlled Polymerization of a Thioglycosidic Monomer

  摘要：

  It is demonstrated that water-soluble, glucosylated poly(pentafluorostyrene) derivatives revealed favorable coating material properties for magnetic iron oxide nanoparticles. To prepare the coating material in high reproducibility and purity as well as in sufficient amounts, a new route of synthesis is established. The preparation and characterization of the glucosylated, tetrafluorostryl monomer, by thiol-para-fluorine "click" reaction, and its polymerization, via nitroxide-mediated radical process, is presented in detail. In addition, the coating material and the resulting particle properties are investigated by means of XPS, DLS, TGA, TEM, and cryo-TEM as well as flow cytometry. The glycopolymer acts as an appropriate stabilizing agent for the superparamagnetic nanoparticles by the formation of an approximately 10 nm thick shell, as shown by the XPS analysis. Furthermore, the application of FITC-labeled glycopolymer yielded fluorescent, superparamagnetic nanoparticles, which can be used for monitoring cell-carbohydrate interactions, because these particles show no cytotoxicity toward 3T3 fibroblasts.

  DOI：

  10.1021/bm101325w