(E)-methyl 3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]prop-2-enoate | 1065269-48-8

• 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: (E)-methyl 3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]prop-2-enoate
• CAS: 1065269-48-8
• 化学式: C₁₉H₂₉N₅O₄Si
• 分子量: 419.556
• InChiKey: MNDLCAKYKOQHOB-CFACAHNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  114.38
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (E)-methyl 3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]prop-2-enoate 在 10% Pd/C 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以94%的产率得到methyl 3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]propanoate
  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：

  3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine 、 甲氧羰基亚甲基三苯基正膦 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(E)-methyl 3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]prop-2-enoate
  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