(2R,3S,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((benzyloxy)methyl)tetrahydrofuran-3-yl acetylglycinate | 1207737-71-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (2R,3S,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((benzyloxy)methyl)tetrahydrofuran-3-yl acetylglycinate
• CAS: 1207737-71-0
• 化学式: C₂₈H₂₈N₆O₆
• 分子量: 544.567
• InChiKey: VPEDYODKIZHVAF-YTFSRNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  146.56
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((benzyloxy)methyl)tetrahydrofuran-3-yl acetylglycinate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以87%的产率得到N-[9-[(2R,4S,5R)-4-羟基-5-(苯基甲氧基甲基)四氢呋喃-2-基]嘌呤-6-基]苯甲酰胺
  参考文献：
  名称：

  Highly stereoselective synthesis of 2′-deoxy-β-ribonucleosides via a 3′-(N-acetyl)-glycyl-directing group

  摘要：

  A facile synthesis of 2'-deoxy-beta-ribonucleosides from 3'-O-(N-acetyl)-glycyl-protected 2'-deoxyribofuranose has been developed. The coupling reactions between the protected 2'-deoxyribose and silylated bases exhibited beta-selectivity up to 98% presumably via a 1',3'-participation mechanism. The 3'-directing group can be introduced and removed easily under mild conditions. This approach provides an efficient and highly stereoselective entry for the synthesis of 2'-deoxy-ribonucleosides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.006
• 作为产物：
  描述：

  [(2R,3S)-5-acetyloxy-2-(phenylmethoxymethyl)oxolan-3-yl] 2-acetamidoacetate 、 N6-苯甲酰基腺嘌呤 在 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 3.0h， 以83%的产率得到(2R,3S,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((benzyloxy)methyl)tetrahydrofuran-3-yl acetylglycinate
  参考文献：
  名称：

  Highly stereoselective synthesis of 2′-deoxy-β-ribonucleosides via a 3′-(N-acetyl)-glycyl-directing group

  摘要：

  A facile synthesis of 2'-deoxy-beta-ribonucleosides from 3'-O-(N-acetyl)-glycyl-protected 2'-deoxyribofuranose has been developed. The coupling reactions between the protected 2'-deoxyribose and silylated bases exhibited beta-selectivity up to 98% presumably via a 1',3'-participation mechanism. The 3'-directing group can be introduced and removed easily under mild conditions. This approach provides an efficient and highly stereoselective entry for the synthesis of 2'-deoxy-ribonucleosides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.006