benzyl onate | 144226-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl onate
• CAS: 144226-39-1
• 化学式: C₃₃H₄₁N₃O₁₂S
• 分子量: 703.767
• InChiKey: WVLKVSZECUGMQK-DEGKTQSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.19
• 重原子数：
  49.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  210.26
• 氢给体数：
  5.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  benzyl onate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以67%的产率得到methyl 5-acetamido-3,5-dideoxy-4-O-(N-((5-(dimethylamino)naphth-1-yl)sulfonyl)glycyl)-D-glycero-α-D-galacto-nonulopyranosidonic acid
  参考文献：
  名称：

  Design and evaluation of a tightly binding fluorescent ligand for influenza A hemagglutinin

  摘要：

  Attachment of influenza virus to susceptible cells is mediated by the viral protein hemagglutinin, which recognizes cell-membrane-bound glycoconjugates that terminate in alpha-sialosides. We have synthesized a fluorescent alpha-sialoside that has the highest affinity of any reported monovalent ligand for hemagglutinin, and it is not a substrate for the viral neuraminidase. This alpha-sialoside provides a convenient fluorescence competition assay for the binding of other ligands. Since each of the currently used binding assays has significant disadvantages, such a simple assay is of great importance for the study of potential inhibitors of viral attachment.

  DOI：

  10.1021/ja00050a004
• 作为产物：
  描述：

  (2R,4S,5R,6R)-5-Acetylamino-6-[(R)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-4-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester 在 4-二甲氨基吡啶 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 80.0h， 生成 benzyl onate
  参考文献：
  名称：

  Design and evaluation of a tightly binding fluorescent ligand for influenza A hemagglutinin

  摘要：

  Attachment of influenza virus to susceptible cells is mediated by the viral protein hemagglutinin, which recognizes cell-membrane-bound glycoconjugates that terminate in alpha-sialosides. We have synthesized a fluorescent alpha-sialoside that has the highest affinity of any reported monovalent ligand for hemagglutinin, and it is not a substrate for the viral neuraminidase. This alpha-sialoside provides a convenient fluorescence competition assay for the binding of other ligands. Since each of the currently used binding assays has significant disadvantages, such a simple assay is of great importance for the study of potential inhibitors of viral attachment.

  DOI：

  10.1021/ja00050a004