1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3-C-(methoxycarbonyl)-D-ribofuranose | 1108175-05-8

• 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: 1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3-C-(methoxycarbonyl)-D-ribofuranose
• CAS: 1108175-05-8
• 化学式: C₂₃H₂₂O₉
• 分子量: 442.422
• InChiKey: YAQLSCXCEUSPIF-UBENBNPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3-C-(methoxycarbonyl)-D-ribofuranose 、 2,6-二氯嘌呤 在 ammonium sulfate 、 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以85%的产率得到2,6-dichloro-9-(2,5-di-O-benzoyl-3-deoxy-3-C-(methoxycarbonyl)-β-D-ribofuranosyl)purine
  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：

  methyl 2,5-di-O-benzoyl-3-deoxy-3-C-(methoxycarbonyl)-β-D-ribofuranoside 、 溶剂黄146 在 硫酸 、 乙酸酐 作用下， 反应 0.5h， 生成 1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3-C-(methoxycarbonyl)-D-ribofuranose
  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