benzyl 3-[9-(tetrahydropyran-2-yl)purin-6-yl]-2-[(tert-butoxycarbonyl)amino]propanoate | 787550-81-6

• 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: benzyl 3-[9-(tetrahydropyran-2-yl)purin-6-yl]-2-[(tert-butoxycarbonyl)amino]propanoate
• 英文别名: benzyl (R,S)-3-[9-(tetrahydropyran-2-yl)purin-6-yl]-2-[(tert-butoxycarbonyl)amino]propanoate；Benzyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[9-(oxan-2-yl)purin-6-yl]propanoate
• CAS: 787550-81-6
• 化学式: C₂₅H₃₁N₅O₅
• 分子量: 481.552
• InChiKey: LAJKOJXKVFCVSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 3-[9-(tetrahydropyran-2-yl)purin-6-yl]-2-[(tert-butoxycarbonyl)amino]propanoate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 9.0h， 生成 2-amino-3-(9H-purin-6-yl)propanoic acid dihydrochloride
  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
• 作为产物：
  描述：

  6-iodo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine 、 benzyl (R,S)-2-[(tert-butoxycarbonyl)amino]-3-iodopropanoate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三(邻甲基苯基)磷 三甲基氯硅烷 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以88%的产率得到benzyl 3-[9-(tetrahydropyran-2-yl)purin-6-yl]-2-[(tert-butoxycarbonyl)amino]propanoate
  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。
• 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.