2-propynyl 3,4,6-tri-O-acetyl-2-deoxy-2-tertbutoxycarbonylamino-β-D-thiogluco-pyranoside | 1261228-67-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-propynyl 3,4,6-tri-O-acetyl-2-deoxy-2-tertbutoxycarbonylamino-β-D-thiogluco-pyranoside
• CAS: 1261228-67-4
• 化学式: C₂₀H₂₉NO₉S
• 分子量: 459.518
• InChiKey: MDIVIYAIHNBGLX-ZKXLYKBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  126.46
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  9-(6-Azidohexyl)-3,6-dibromocarbazole 、 2-propynyl 3,4,6-tri-O-acetyl-2-deoxy-2-tertbutoxycarbonylamino-β-D-thiogluco-pyranoside 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 以98%的产率得到[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-6-[[1-[6-(3,6-dibromocarbazol-9-yl)hexyl]triazol-4-yl]methylsulfanyl]-5-[(2-methylpropan-2-yl)oxycarbonylamino]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Water-soluble conjugated polyelectrolyte with pendant glycocluster: Synthesis and its interaction with heparin

  摘要：

  A novel fluorescent conjugated polyelectrolyte with pendant glucosamine hydrochloride clusters was prepared through Cu(I)-catalyzed azide/alkyne "click" ligation and Suzuki coupling polymerization. Compared with monosugar-functionalized conjugated polymer, the water-solubility and fluorescence quantum yield of the glycocluster-containing polymer (P-3) were significantly improved. As a glucosamine-containing cationic fluorescent polyelectrolyte, the water-soluble fluorescent polymer can interact with heparin through electrostatic bindings, which induce great fluorescence quenching of P-3 due to the polymer aggregation. Furthermore, upon treatment of the P-3 heparin ensemble with protamine, the fluorescence emission of P-3 recovered since the protamine possesses a competitively strong binding affinity to the heparin and thus results in the release of the fluorescent glycopolymer P-3 from the P-3 heparin ensemble. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2010.11.048
• 作为产物：
  描述：

  propargyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium methylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-propynyl 3,4,6-tri-O-acetyl-2-deoxy-2-tertbutoxycarbonylamino-β-D-thiogluco-pyranoside
  参考文献：
  名称：

  Water-soluble conjugated polyelectrolyte with pendant glycocluster: Synthesis and its interaction with heparin

  摘要：

  A novel fluorescent conjugated polyelectrolyte with pendant glucosamine hydrochloride clusters was prepared through Cu(I)-catalyzed azide/alkyne "click" ligation and Suzuki coupling polymerization. Compared with monosugar-functionalized conjugated polymer, the water-solubility and fluorescence quantum yield of the glycocluster-containing polymer (P-3) were significantly improved. As a glucosamine-containing cationic fluorescent polyelectrolyte, the water-soluble fluorescent polymer can interact with heparin through electrostatic bindings, which induce great fluorescence quenching of P-3 due to the polymer aggregation. Furthermore, upon treatment of the P-3 heparin ensemble with protamine, the fluorescence emission of P-3 recovered since the protamine possesses a competitively strong binding affinity to the heparin and thus results in the release of the fluorescent glycopolymer P-3 from the P-3 heparin ensemble. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2010.11.048