(2RS,5S)-N-{9-[5-benzyl-5-(hydroxymethyl)tetrahydrofuran-2-yl]-9H-purin-6-yl}benzamide | 1024613-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (2RS,5S)-N-{9-[5-benzyl-5-(hydroxymethyl)tetrahydrofuran-2-yl]-9H-purin-6-yl}benzamide
• CAS: 1024613-26-0
• 化学式: C₂₄H₂₃N₅O₃
• 分子量: 429.478
• InChiKey: IQCQVSQFXRUBOA-WIIYFNMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  102.16
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2RS,5S)-N-{9-[5-benzyl-5-(hydroxymethyl)tetrahydrofuran-2-yl]-9H-purin-6-yl}benzamide 在 氨 作用下， 以 甲醇 为溶剂， 生成 [(2S,5S)-5-(6-aminopurin-9-yl)-2-benzyloxolan-2-yl]methanol 、 [(2S,5R)-5-(6-aminopurin-9-yl)-2-benzyloxolan-2-yl]methanol
  参考文献：
  名称：

  Asymmetric synthesis of 4′-C-benzyl-2′,3′-dideoxynucleoside analogues from 3-benzyl-2-hydroxy-2-cyclopenten-1-one

  摘要：

  Both enantiomers of the key intermediate, 2-benzyl-5-oxo-tetrahydro-furan-2-carboxylic acid were obtained by asymmetric oxidation of 3 -benzyl-2-hyd roxy-2-cyclopen ten- 1 -one with all ee >= 96%, using the tartaric ester/Ti(OiPr)(4)/t-BuOOH complex, and transformed to the corresponding 4'-substituted nucleoside analogues with up to 61% overall yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.028
• 作为产物：
  描述：

  (2RS,5S)-N-{9-[5-benzyl-5-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl]-9H-purin-6-yl}benzamide 在 四丁基氟化铵 作用下， 反应 2.0h， 以100%的产率得到(2RS,5S)-N-{9-[5-benzyl-5-(hydroxymethyl)tetrahydrofuran-2-yl]-9H-purin-6-yl}benzamide
  参考文献：
  名称：

  Asymmetric synthesis of 4′-C-benzyl-2′,3′-dideoxynucleoside analogues from 3-benzyl-2-hydroxy-2-cyclopenten-1-one

  摘要：

  Both enantiomers of the key intermediate, 2-benzyl-5-oxo-tetrahydro-furan-2-carboxylic acid were obtained by asymmetric oxidation of 3 -benzyl-2-hyd roxy-2-cyclopen ten- 1 -one with all ee >= 96%, using the tartaric ester/Ti(OiPr)(4)/t-BuOOH complex, and transformed to the corresponding 4'-substituted nucleoside analogues with up to 61% overall yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.028