5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylcytidine | 470700-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylcytidine
• 英文别名: S-[2-(2-bromophenyl)-2-methylpropyl] (2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-[diethoxy(oxido)phosphaniumyl]oxy-2-(phenylmethoxymethyl)oxolane-2-carbothioate
• CAS: 470700-00-6
• 化学式: C₃₁H₃₉BrN₃O₈PS
• 分子量: 724.61
• InChiKey: DOOJWZGKWSUYEK-ZRLKGHKBSA-N

物化性质

• 沸点：
  769.1±70.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  45
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  170
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylcytidine 在 三正丁基氢锡 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 磷酸二乙酯 、 2,3-dihydro-3,3-dimethylbenzo[b]thiophene 、 5'β-O-benzyl-2'-deoxy-3'-O-diethylphosphorylcytidine 、 5'α-O-benzyl-2'-deoxy-3'-O-diethylphosphorylcytidine
  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：

  在 2,6-二甲基吡啶 、 碘 、 三氟乙酸 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]-2'-deoxy-3'-O-diethylphosphorylcytidine
  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

文献信息

• The effect of the base in the fragmentation of nucleotide C4′ radicals
  作者：David Crich、Dae-Hwan Suk、Xiaolin Hao

  DOI：10.1016/s0040-4020(02)00557-4

  日期：2002.7

  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.