(2R,3R,4S)-2-(6-(benzamido)-9H-purin-9-yl)-4-(benzyloxy)-tetrahydrofuran-3-yl acetate | 1333503-54-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S)-2-(6-(benzamido)-9H-purin-9-yl)-4-(benzyloxy)-tetrahydrofuran-3-yl acetate
• CAS: 1333503-54-0
• 化学式: C₂₅H₂₃N₅O₅
• 分子量: 473.488
• InChiKey: RGVZBDIHEWNTCG-PIBDYAPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  117.46
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-2-(6-(benzamido)-9H-purin-9-yl)-4-(benzyloxy)-tetrahydrofuran-3-yl acetate 在 甲醇 、 氨 作用下， 反应 48.0h， 以95%的产率得到(2R,3R,4S)-2-(6-amino-9H-purin-9-yl)-4-(benzyloxy)-tetrahydrofuran-3-ol
  参考文献：
  名称：

  Synthesis and antiviral evaluation of α-l-2′-deoxythreofuranosyl nucleosides

  摘要：

  The synthesis of a series of alpha-L-2'-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-alpha-L-threose, involving a Vorbruggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleoside phosphate prodrug of the T analogue, were evaluated against a broad panel of different viruses but found inactive, while also lacking notable cellular toxicity. The thymidine analogue showed inhibition to mitochondrial thymidine kinase-2 (TK-2), herpes simplex virus type 1 (HSV-1) TK, varicella-zoster virus (VZV) TK and Mycobacterium tuberculosis thymidylate kinase. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.036
• 作为产物：
  描述：

  (3R,4S)-4-(benzyloxy)-tetrahydrofuran-2,3-diyl diacetate 、 N-Benzoyl-N,9-bis(trimethylsilyl)adenin 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 24.0h， 以0.68 g的产率得到(2R,3R,4S)-2-(6-(benzamido)-9H-purin-9-yl)-4-(benzyloxy)-tetrahydrofuran-3-yl acetate
  参考文献：
  名称：

  Synthesis and antiviral evaluation of α-l-2′-deoxythreofuranosyl nucleosides

  摘要：

  The synthesis of a series of alpha-L-2'-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-alpha-L-threose, involving a Vorbruggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleoside phosphate prodrug of the T analogue, were evaluated against a broad panel of different viruses but found inactive, while also lacking notable cellular toxicity. The thymidine analogue showed inhibition to mitochondrial thymidine kinase-2 (TK-2), herpes simplex virus type 1 (HSV-1) TK, varicella-zoster virus (VZV) TK and Mycobacterium tuberculosis thymidylate kinase. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.036