5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-6-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphoryladenosine | 470699-91-3

• 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: 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-6-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphoryladenosine
• CAS: 470699-91-3
• 化学式: C₃₇H₄₇BrN₅O₉PS
• 分子量: 848.752
• InChiKey: MDGSHGAPRGGJLP-DBWZWNDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.61
• 重原子数：
  54.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  162.22
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-6-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphoryladenosine 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以79%的产率得到5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphoryladenosine
  参考文献：
  名称：

  The effect of the base in the fragmentation of nucleotide C4′ radicals

  摘要：

  A series of 3'-O-diethylphosphoryl-4'-alpha-[(2-halophenylethylthio)carbonyl] substituted esters of thymidine, cytidine, adenosine and guanosine are prepared by total synthesis and used as C4'-radical precursors in a competition kinetic method using tributyltin hydride as the reductant. The pseudo-first order rate constants for the C4'-radicals so generated decrease in the order guansoine>cytidine>adenosine>thymidine with that for guanosine being too rapid for determination by the present competition kinetic method. A (119)Sn NMR method is presented for estimation of the purity of tin hydride solutions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00557-4
• 作为产物：
  描述：

  2-(2-bromophenyl)-2-methylpropanethiol 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 碘 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-6-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphoryladenosine
  参考文献：
  名称：

  The effect of the base in the fragmentation of nucleotide C4′ radicals

  摘要：

  A series of 3'-O-diethylphosphoryl-4'-alpha-[(2-halophenylethylthio)carbonyl] substituted esters of thymidine, cytidine, adenosine and guanosine are prepared by total synthesis and used as C4'-radical precursors in a competition kinetic method using tributyltin hydride as the reductant. The pseudo-first order rate constants for the C4'-radicals so generated decrease in the order guansoine>cytidine>adenosine>thymidine with that for guanosine being too rapid for determination by the present competition kinetic method. A (119)Sn NMR method is presented for estimation of the purity of tin hydride solutions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00557-4