[(2R,3R,4S,5R)-4-benzoyloxy-5-[2-chloro-6-(methylamino)purin-9-yl]-3-fluorooxolan-2-yl]methyl benzoate | 551929-60-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: [(2R,3R,4S,5R)-4-benzoyloxy-5-[2-chloro-6-(methylamino)purin-9-yl]-3-fluorooxolan-2-yl]methyl benzoate
• CAS: 551929-60-3
• 化学式: C₂₅H₂₁ClFN₅O₅
• 分子量: 525.924
• InChiKey: BHMAZGBOVQQAIP-VALFRTSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R)-4-benzoyloxy-5-[2-chloro-6-(methylamino)purin-9-yl]-3-fluorooxolan-2-yl]methyl benzoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以97%的产率得到(2R,3S,4S,5R)-2-(2-Chloro-6-(methylamino)-9H-purin-9-yl)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Design, synthesis and binding affinity of 3′-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands

  摘要：

  Several 3'-fluoro analogues, la, 1b, and le of selective and potent adenosine A(3) receptor agonist, Cl-IB-MECA were synthesized from D-xylose via highly regioselective opening of lyxo-epoxides, 8a and 811 with fluoride anion. Compared to the high binding affinity of Cl-IB-MECA to the A(3) adenosine receptor, the corresponding 3-fluoro derivative showed remarkably decreased binding affinity, indicating that 3'-hydroxyl group acts as hydrogen bonding acceptor, not hydrogen bonding donor like fluorine atom in binding to the A(3) adenosine receptor. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00027-1
• 作为产物：
  描述：

  methyl 5-O-benzoyl-3-deoxy-3-fluoro-β-D-ribofuranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 13.25h， 生成 [(2R,3R,4S,5R)-4-benzoyloxy-5-[2-chloro-6-(methylamino)purin-9-yl]-3-fluorooxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  Design, synthesis and binding affinity of 3′-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands

  摘要：

  Several 3'-fluoro analogues, la, 1b, and le of selective and potent adenosine A(3) receptor agonist, Cl-IB-MECA were synthesized from D-xylose via highly regioselective opening of lyxo-epoxides, 8a and 811 with fluoride anion. Compared to the high binding affinity of Cl-IB-MECA to the A(3) adenosine receptor, the corresponding 3-fluoro derivative showed remarkably decreased binding affinity, indicating that 3'-hydroxyl group acts as hydrogen bonding acceptor, not hydrogen bonding donor like fluorine atom in binding to the A(3) adenosine receptor. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00027-1