5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-9-(β-D-ribofuranosyl)-2-[2-(triphenylmethylthio)ethyl]aminopurine | 1334122-46-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-9-(β-D-ribofuranosyl)-2-[2-(triphenylmethylthio)ethyl]aminopurine
• CAS: 1334122-46-1
• 化学式: C₅₈H₆₃N₅O₆SSi
• 分子量: 986.32
• InChiKey: ZUXWPOPUTWRSEF-KKSZRBGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.64
• 重原子数：
  71.0
• 可旋转键数：
  19.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  122.01
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-9-(β-D-ribofuranosyl)-2-[2-(triphenylmethylthio)ethyl]aminopurine 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以79%的产率得到5'-O-(4,4'-dimethoxytrityl)-3'-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphino]-2'-O-(tert-butyldimethylsilyl)-9-(β-D-ribofuranosyl)-2-[2-(triphenylmethylthio)ethyl]aminopurine
  参考文献：
  名称：

  Covalent stabilization of a small molecule–RNA complex

  摘要：

  We demonstrate covalent bond formation between an RNA aptamer containing a cysteamine-tethered nucleobase and helix-threading peptides (HTPs) containing alpha-bromoacetamide N-termini. The reaction is high yielding and inhibited by a DNA strand Watson-Crick complementary to the aptamer sequence indicating covalent reaction is dependent on the high affinity HTP-binding site present in the folded aptamer. These results are important for future structural studies of HTP-RNA complexes and methods for the discovery of new high affinity analogs via covalent tethering strategies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.136
• 作为产物：
  描述：

  在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 氨 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-9-(β-D-ribofuranosyl)-2-[2-(triphenylmethylthio)ethyl]aminopurine
  参考文献：
  名称：

  Covalent stabilization of a small molecule–RNA complex

  摘要：

  We demonstrate covalent bond formation between an RNA aptamer containing a cysteamine-tethered nucleobase and helix-threading peptides (HTPs) containing alpha-bromoacetamide N-termini. The reaction is high yielding and inhibited by a DNA strand Watson-Crick complementary to the aptamer sequence indicating covalent reaction is dependent on the high affinity HTP-binding site present in the folded aptamer. These results are important for future structural studies of HTP-RNA complexes and methods for the discovery of new high affinity analogs via covalent tethering strategies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.136