3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-N-methoxy-N-methylpropanamide | 1065269-52-4

• 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: 3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-N-methoxy-N-methylpropanamide
• CAS: 1065269-52-4
• 化学式: C₂₀H₃₄N₆O₄Si
• 分子量: 450.613
• InChiKey: IXNNETWMGJAQJE-IJEWVQPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  117.62
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-N-methoxy-N-methylpropanamide 在 苯基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以71%的产率得到3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-1-phenylpropan-1-one
  参考文献：
  名称：

  Synthesis and evaluation of 5′-modified 2′-deoxyadenosine analogues as anti-hepatitis C virus agents

  摘要：

  In order to study the effect of 5'-modification of 2'-deoxynucleoside on its anti-HCV activity, several analogues were synthesized and evaluated. Among the analogues, a 5'-deoxy-5'-phenacylated analogue exhibited a good anti-HCV activity with an EC(50) of 15.1 mu M. This compound is expected to operate via a type of mechanism that does not involve a generally known 5'-O-triphosphorylation process. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.015
• 作为产物：
  描述：

  methyl 3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]propanoate 、 二甲羟胺盐酸盐 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以96%的产率得到3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-N-methoxy-N-methylpropanamide
  参考文献：
  名称：

  Synthesis and evaluation of 5′-modified 2′-deoxyadenosine analogues as anti-hepatitis C virus agents

  摘要：

  In order to study the effect of 5'-modification of 2'-deoxynucleoside on its anti-HCV activity, several analogues were synthesized and evaluated. Among the analogues, a 5'-deoxy-5'-phenacylated analogue exhibited a good anti-HCV activity with an EC(50) of 15.1 mu M. This compound is expected to operate via a type of mechanism that does not involve a generally known 5'-O-triphosphorylation process. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.015