5'-O-benzyl-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}adenosine | 470700-01-7

• 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-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}adenosine
• 英文别名: S-[2-(2-iodophenyl)ethyl] (2R,3S,5R)-5-(6-aminopurin-9-yl)-3-[diethoxy(oxido)phosphaniumyl]oxy-2-(phenylmethoxymethyl)oxolane-2-carbothioate
• CAS: 470700-01-7
• 化学式: C₃₀H₃₅IN₅O₇PS
• 分子量: 767.581
• InChiKey: BPENGIBMFWFXJN-NHWZYIIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  45
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  181
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5'-O-benzyl-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}adenosine 在 三正丁基氢锡 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 2,3-二氢苯并[b]噻吩 、 5'β-O-benzyl-2'-deoxy-3'-O-diethylphosphoryladenosine 、 5'α-O-benzyl-2'-deoxy-3'-O-diethylphosphoryladenosine 、 5'-O-benzyl-2'-deoxy-3'-O-diethylphosphoryl-4'α-(2-phenylethylthiocarbonyl)adenosine
  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：

  5'-O-benzyl-6-N-(tert-butyloxycarbonyl)-2'-deoxy-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}adenosine 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 碘 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 0.83h， 生成 5'-O-benzyl-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}adenosine
  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