(2S)-2-[(6-chloro-9H-purin-2-yl)amino]-3-phenyl-1-propanol | 690267-69-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-2-[(6-chloro-9H-purin-2-yl)amino]-3-phenyl-1-propanol
• 英文别名: (2S)-2-[(6-chloro-7H-purin-2-yl)amino]-3-phenylpropan-1-ol
• CAS: 690267-69-7
• 化学式: C₁₄H₁₄ClN₅O
• 分子量: 303.751
• InChiKey: LDHNYSCKGIAXGH-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  86.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(6-chloro-9H-purin-2-yl)amino]-3-phenyl-1-propanol 在 三氟甲磺酸三甲基硅酯 N,O-双三甲硅基乙酰胺 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.0h， 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
• 作为产物：
  描述：

  2-((S)-1-Hydroxymethyl-2-phenyl-ethylamino)-9H-purin-6-ol 在 甲醇 、 4-二甲氨基吡啶 、 四乙基氯化铵 、 potassium carbonate 、 N,N-二甲基苯胺 、 三乙胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.17h， 生成 (2S)-2-[(6-chloro-9H-purin-2-yl)amino]-3-phenyl-1-propanol
  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

文献信息

• Efficient Synthesis of an Adenosine A2a Agonist:  Glycosylation of 2-Haloadenines and an <i>N</i>²-Alkyl-6-chloroguanine
  作者：John M. Caddell、Alan M. Chapman、Bob E. Cooley、Brian P. Downey、Michael P. LeBlanc、Mary M. Jackson、Thomas M. O'Connell、Hahn-My Phung、Thomas D. Roper、Shiping Xie

  DOI：10.1021/jo049963x

  日期：2004.4.1

  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.