methyl (2S,3R,4R,5R)-4-(benzoyloxy)-2-((benzoyloxy)methyl)-5-(2-chloro-6-(methylamino)-9H-purin-9-yl)tetrahydrofuran-3-carboxylate | 1108175-15-0

• 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: methyl (2S,3R,4R,5R)-4-(benzoyloxy)-2-((benzoyloxy)methyl)-5-(2-chloro-6-(methylamino)-9H-purin-9-yl)tetrahydrofuran-3-carboxylate
• CAS: 1108175-15-0
• 化学式: C₂₇H₂₄ClN₅O₇
• 分子量: 565.97
• InChiKey: XAPTYEAIIXXWBL-IVKZONNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  143.76
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R,4R,5R)-4-(benzoyloxy)-2-((benzoyloxy)methyl)-5-(2-chloro-6-(methylamino)-9H-purin-9-yl)tetrahydrofuran-3-carboxylate 、 甲胺 以 四氢呋喃 、 水 为溶剂， 以23%的产率得到2-chloro-N⁶-methyl-9-(3-C-(methylcarbamoyl)-3-deoxy-β-D-ribofuranosyl)adenine
  参考文献：
  名称：

  Synthesis of 3′-Acetamidoadenosine Derivatives as Potential A₃Adenosine Receptor Agonists

  摘要：

  On the basis of high binding affinity of 3'-aminoadenosine derivatives 2b at the human A(3) adenosine receptor (AR), 3'-acetamidoadenosine derivatives 3a-e were synthesized from 1,2:5,6-di-O-isopropylidene-D-glucose via stereoselective hydroboration as a key step. Although all synthesized compounds were totally devoid of binding affinity at the human A(3)AR, our results revealed that 3'-position of adenosine can only be tolerated with small size of a hydrogen bonding donor like hydroxyl or amino group in the binding site of human A(3)AR.

  DOI：

  10.1080/15257770801944436
• 作为产物：
  描述：

  2,6-dichloro-9-(2,5-di-O-benzoyl-3-deoxy-3-C-(methoxycarbonyl)-β-D-ribofuranosyl)purine 、 methylamine acetate 以 四氢呋喃 为溶剂， 以96%的产率得到methyl (2S,3R,4R,5R)-4-(benzoyloxy)-2-((benzoyloxy)methyl)-5-(2-chloro-6-(methylamino)-9H-purin-9-yl)tetrahydrofuran-3-carboxylate
  参考文献：
  名称：

  Synthesis of 3′-Acetamidoadenosine Derivatives as Potential A₃Adenosine Receptor Agonists

  摘要：

  On the basis of high binding affinity of 3'-aminoadenosine derivatives 2b at the human A(3) adenosine receptor (AR), 3'-acetamidoadenosine derivatives 3a-e were synthesized from 1,2:5,6-di-O-isopropylidene-D-glucose via stereoselective hydroboration as a key step. Although all synthesized compounds were totally devoid of binding affinity at the human A(3)AR, our results revealed that 3'-position of adenosine can only be tolerated with small size of a hydrogen bonding donor like hydroxyl or amino group in the binding site of human A(3)AR.

  DOI：

  10.1080/15257770801944436