5-bromo-1-(β-D-2',3',5'-tri-O-acetylarabinofuranosyl)uracil | 105659-31-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-bromo-1-(β-D-2',3',5'-tri-O-acetylarabinofuranosyl)uracil
• 英文别名: [(2R,3R,4S,5R)-3,4-diacetyloxy-5-(5-bromo-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 105659-31-2
• 化学式: C₁₅H₁₇BrN₂O₉
• 分子量: 449.212
• InChiKey: OVWGEZUVGHETAU-NRWUCQMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-bromo-1-(β-D-2',3',5'-tri-O-acetylarabinofuranosyl)uracil 在 tetraphosphorus decasulfide 、 DMd 、 氨 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 生成 5-bromo-O⁴-methyl-1-(β-D-arabinofuranosyl)pyrimidin-2(1H)-one
  参考文献：
  名称：

  Synthesis, Cytotoxic Effect and Antiviral Activity of 1-(β-D-Arabinofuranosyl)-5-Bromo-N⁴-Substitutedcytosine and 1-(β-D-Arabinofuranosyl)-5-Bromo-4-Methoxypyrimidin-2(1h)-One Derivatives

  摘要：

  A convenient and mild synthesis of 5-bromo-N-4-substituted-1-(beta-D-arabinofuranosyl)cytosine and 5-bromo-O-4-methyl-1-(beta-D-arabinofuranosyl)pyrimidin-2(1H)-one derivatives by selective oxyfunctionalization of the corresponding 4-thionucleosides with 3,3-dimethyldioxirane is reported. The cytotoxicity and the antiviral activity against parainfluenza 1 (Sendai virus) of all new synthesized products are also reported.

  DOI：

  10.1080/07328319908044622
• 作为产物：
  描述：

  5-溴尿苷 在 吡啶 、 碳酸二苯酯 、 碳酸氢钠 、 三乙胺 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 29.5h， 生成 5-bromo-1-(β-D-2',3',5'-tri-O-acetylarabinofuranosyl)uracil
  参考文献：
  名称：

  Synthesis, Cytotoxic Effect and Antiviral Activity of 1-(β-D-Arabinofuranosyl)-5-Bromo-N⁴-Substitutedcytosine and 1-(β-D-Arabinofuranosyl)-5-Bromo-4-Methoxypyrimidin-2(1h)-One Derivatives

  摘要：

  A convenient and mild synthesis of 5-bromo-N-4-substituted-1-(beta-D-arabinofuranosyl)cytosine and 5-bromo-O-4-methyl-1-(beta-D-arabinofuranosyl)pyrimidin-2(1H)-one derivatives by selective oxyfunctionalization of the corresponding 4-thionucleosides with 3,3-dimethyldioxirane is reported. The cytotoxicity and the antiviral activity against parainfluenza 1 (Sendai virus) of all new synthesized products are also reported.

  DOI：

  10.1080/07328319908044622

文献信息

• Bromination at C-5 of pyrimidine and C-8 of purine nucleosides with 1,3-dibromo-5,5-dimethylhydantoin
  作者：Ramanjaneyulu Rayala、Stanislaw F. Wnuk

  DOI：10.1016/j.tetlet.2012.04.081

  日期：2012.6

  Treatment of the protected and unprotected nucleosides with 1,3-dibromo-5,5-dimethylhydantoin in aprotic solvents such as CH2Cl2, CH3CN, or DMF effected smooth bromination of uridine and cytidine derivatives at C-5 of pyrimidine rings as well as adenosine and guanosine derivatives at C-8 of purine rings. Addition of Lewis acids such as trimethylsilyl trifluoromethanesulfonate enhanced the efficiency of bromination. (C) 2012 Elsevier Ltd. All rights reserved.