N-9-(2-benzyloxycarbonylethyl)adenine | 183181-59-1

• 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: N-9-(2-benzyloxycarbonylethyl)adenine
• CAS: 183181-59-1
• 化学式: C₁₅H₁₅N₅O₂
• 分子量: 297.316
• InChiKey: JPXKQKGLMKTUAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  95.92
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-9-(2-benzyloxycarbonylethyl)adenine 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 lithium hydroxide monohydrate 、 三甲基溴硅烷 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 30.0h， 生成 (R)-(4-(6-amino-9H-purin-9-yl)-2-hydroxybutyl)phosphonic acid disodium salt
  参考文献：
  名称：

  Synthesis of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA)

  摘要：

  A synthetic pathway to new acyclonucleoside phosphonates, as analogues of Adefovir, is described. The reduction of an acyclonucleoside beta-ketophosphonate, readily available from the nucleobase and benzyl-acrylate, afforded a mixture of (R)- and (S)-beta-hydroxyphosphonate derivatives which was resolved. The assignment of the absolute configuration was proposed on the basis of NMR studies and was supported by molecular modelling studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.010
• 作为产物：
  描述：

  丙烯酸苄酯 、 腺嘌呤 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以77%的产率得到N-9-(2-benzyloxycarbonylethyl)adenine
  参考文献：
  名称：

  Synthesis of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA)

  摘要：

  A synthetic pathway to new acyclonucleoside phosphonates, as analogues of Adefovir, is described. The reduction of an acyclonucleoside beta-ketophosphonate, readily available from the nucleobase and benzyl-acrylate, afforded a mixture of (R)- and (S)-beta-hydroxyphosphonate derivatives which was resolved. The assignment of the absolute configuration was proposed on the basis of NMR studies and was supported by molecular modelling studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.010