(2R,3R,4R,5R)-2-(6-amino-2-{[(1S)-2-hydroxy-1-(phenylmethyl)ethyl]amino}-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate | 252719-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2R,3R,4R,5R)-2-(6-amino-2-{[(1S)-2-hydroxy-1-(phenylmethyl)ethyl]amino}-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate
• CAS: 252719-85-0
• 化学式: C₂₅H₃₀N₁₀O₆
• 分子量: 566.577
• InChiKey: MYPYTUJPFRHXOF-AYQBYMDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  207.31
• 氢给体数：
  3.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2-(6-amino-2-{[(1S)-2-hydroxy-1-(phenylmethyl)ethyl]amino}-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate 在 甲醇 、 potassium carbonate 作用下， 生成 GW328267X
  参考文献：
  名称：

  Efficient Synthesis of an Adenosine A2a Agonist:  Glycosylation of 2-Haloadenines and an N²-Alkyl-6-chloroguanine

  摘要：

  A convergent synthesis of adenosine A2a agonist 1 in the form of its maleate salt 2 was achieved. The key step in this approach was the highly selective 9beta-glycosylation reaction between 2-haloadenines or an N-2-alkyl-6-chloroguanine and a D-ribose derivative containing a 2-ethyltetrazolyl moiety. Glycosylations of other purine derivatives were also examined, and the methods developed provide efficient access to a variety of adenosine analogues such as 2-alkylaminoadenosines, an attractive class of compounds with antiinflammatory activity.

  DOI：

  10.1021/jo049963x
• 作为产物：
  描述：

  5-[(3aR,4R,6R,6aR)-2,2-dimethyl-6-(methyloxy)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-ethyl-2H-tetrazole 在 三氟甲磺酸三甲基硅酯 吡啶 、 甲醇 、 N,O-双三甲硅基乙酰胺 、 硫酸 、 乙酰氯 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 4.0h， 生成 (2R,3R,4R,5R)-2-(6-amino-2-{[(1S)-2-hydroxy-1-(phenylmethyl)ethyl]amino}-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate
  参考文献：
  名称：

  Efficient Synthesis of an Adenosine A2a Agonist:  Glycosylation of 2-Haloadenines and an N²-Alkyl-6-chloroguanine

  摘要：

  A convergent synthesis of adenosine A2a agonist 1 in the form of its maleate salt 2 was achieved. The key step in this approach was the highly selective 9beta-glycosylation reaction between 2-haloadenines or an N-2-alkyl-6-chloroguanine and a D-ribose derivative containing a 2-ethyltetrazolyl moiety. Glycosylations of other purine derivatives were also examined, and the methods developed provide efficient access to a variety of adenosine analogues such as 2-alkylaminoadenosines, an attractive class of compounds with antiinflammatory activity.

  DOI：

  10.1021/jo049963x