3-(9-benzylpurin-6-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid | 787550-86-1

• 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: 3-(9-benzylpurin-6-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid
• 英文别名: (R,S)-3-(9-benzylpurin-6-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid；3-(9-Benzylpurin-6-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 787550-86-1
• 化学式: C₂₀H₂₃N₅O₄
• 分子量: 397.434
• InChiKey: BJOMXEJGRPWUCO-UHFFFAOYSA-N

物化性质

• 熔点：
  172-175 °C
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(9-benzylpurin-6-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 8.0h， 以84%的产率得到2-amino-3-(9-benzylpurin-6-yl)propanoic acid hydrochloride
  参考文献：
  名称：

  [EN] (PURIN-6-YL) AMINO ACID AND PRODUCTION METHOD THEREOF
  [FR] ACIDES (PURIN-6-YL) AMINES ET PROCEDE DE FABRICATION

  摘要：

  本发明提供了一种合成(嘌呤-6-基)氨基酸的方法，该方法可用作抗癌、抗病毒剂等药物或其中间体。在Pd2dba3、三苯基胂和碘化铜的存在下，通过使9-苄基-6-碘嘌呤与甲基(R，S)-2-[(t-丁氧羰基)氨基]-3-[4-(三甲基基锡)苯基]丙酸酯反应，可制得甲基(R，S)-3-[4-(9-苄基嘌呤-6-基)苯基]-2-[(t-丁氧羰基)氨基]丙酸酯。

  公开号：

  WO2004094426A1
• 作为产物：
  描述：

  9-苄基-6-碘嘌呤 在 palladium on activated charcoal 三甲基氯硅烷 、 氢气 、 锌 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.67h， 生成 3-(9-benzylpurin-6-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid
  参考文献：
  名称：

  A Facile and Efficient Synthesis of (Purin-6-yl)alanines

  摘要：

  (Purin-6-yl)alanines, a new class of amino acid-nucleobase conjugates, were synthesized by palladium-catalyzed cross-coupling reactions of protected iodozincalanines with 6-iodopurines (9-Bn-6-iodopurine and 9-THP-6-iodopurine as well as acyl-protected 6-iodopurine ribonucleoside and 2-deoxyribonucleoside). Free purine base and nucleosides bearing alanine in position 6 were obtained after complete deprotection of the products of cross-coupling reactions.

  DOI：

  10.1021/jo048812r

文献信息

• [EN] (PURIN-6-YL) AMINO ACID AND PRODUCTION METHOD THEREOF<br/>[FR] ACIDES (PURIN-6-YL) AMINES ET PROCEDE DE FABRICATION
  申请人：USTAV ORGANICKE CHEMIE A BIOCH

  公开号：WO2004094426A1

  公开（公告）日：2004-11-04

  The invention provides a synthetic method of (purin-6-yl)amino acids which are useful as medicaments of anticancer, anti-virus agents and so on or their intermediates. Methyl (R, S)-3-[4-(9-benzylpurin-6-yl) phenyl]-2-[ (t-butoxycarbonyl) amino] propanoate is produced by making 9-benzyl-6-iodopurine react with methyl (R, S)-2-[ (t-butoxycarbonyl) amino]-3-[4-(trimethylstananyl) phenyl] propionate in the presence of Pd2dba3, triphenylarsine and copper iodide.

  本发明提供了一种合成(嘌呤-6-基)氨基酸的方法，该方法可用作抗癌、抗病毒剂等药物或其中间体。在Pd2dba3、三苯基胂和碘化铜的存在下，通过使9-苄基-6-碘嘌呤与甲基(R，S)-2-[(t-丁氧羰基)氨基]-3-[4-(三甲基基锡)苯基]丙酸酯反应，可制得甲基(R，S)-3-[4-(9-苄基嘌呤-6-基)苯基]-2-[(t-丁氧羰基)氨基]丙酸酯。
• (Purin-6-yl) amino acid and production method thereof
  申请人：Hocek Michal

  公开号：US20060128956A1

  公开（公告）日：2006-06-15

  The invention provides a synthetic method of (purin-6-yl)amino acids which are useful as medicaments of anticancer, anti-virus agents and so on or their intermediates. Methyl (R,S)-3-[4-(9-benzylpurin-6-yl) phenyl]-2-[(t-butoxycarbonyl) amino]propanoate is produced by making 9-benzyl-6-iodopurine react with methyl (R,S)-2-[(t-butoxycarbonyl)amino]-3-[4-(trimethyl-stananyl) phenyl]propionate in the presence of Pd 2 dba 3 , triphenylarsine and copper iodide.

  本发明提供了一种合成（嘌呤-6-基）氨基酸的方法，它们可用作抗癌、抗病毒药物等药物或它们的中间体。通过使9-苄基-6-碘嘌呤在Pd2dba3、三苯基胂和碘化铜的存在下与甲基（R，S）-2-[(t-丁氧羰基)氨基]-3-[4-(三甲基基锡基)苯基]丙酸酯反应，可制得甲基（R，S）-3-[4-(9-苄基嘌呤-6-基)苯基]-2-[(t-丁氧羰基)氨基]丙酸酯。
• EP1615926A1
  申请人：——

  公开号：EP1615926A1

  公开（公告）日：2006-01-18
• A Facile and Efficient Synthesis of (Purin-6-yl)alanines
  作者：Petr Čapek、Radek Pohl、Michal Hocek

  DOI：10.1021/jo048812r

  日期：2004.11.1

  (Purin-6-yl)alanines, a new class of amino acid-nucleobase conjugates, were synthesized by palladium-catalyzed cross-coupling reactions of protected iodozincalanines with 6-iodopurines (9-Bn-6-iodopurine and 9-THP-6-iodopurine as well as acyl-protected 6-iodopurine ribonucleoside and 2-deoxyribonucleoside). Free purine base and nucleosides bearing alanine in position 6 were obtained after complete deprotection of the products of cross-coupling reactions.