1-(2-bromo-1-C-cyano-2-deoxy-3,5-di-O-t-butyldimethylsilyl-β-D-arabino-pentofuranosyl)-5-iodouracil | 167023-14-5

• 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: 1-(2-bromo-1-C-cyano-2-deoxy-3,5-di-O-t-butyldimethylsilyl-β-D-arabino-pentofuranosyl)-5-iodouracil
• CAS: 167023-14-5
• 化学式: C₂₂H₃₇BrIN₃O₅Si₂
• 分子量: 686.532
• InChiKey: GPQSHOHIGQXIMJ-DBHNTLKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  106.34
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-(2-bromo-1-C-cyano-2-deoxy-3,5-di-O-t-butyldimethylsilyl-β-D-arabino-pentofuranosyl)-5-iodouracil 在 ammonium bifluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以47%的产率得到1-(2-bromo-1-C-cyano-2-deoxy-β-D-arabino-pentofuranosyl)-5-iodouracil
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 1′-C-Cyano-Pyrimidine Nucleosides

  摘要：

  2'-Deoxy-, 2'-bromo-, and arabine-1'-C-cyano-pyrimidine nucleosides were synthesized from O-2,2'-cyclouridine. Incorporation of cyano group at the anomeric position was achieved by treatment of 1',2'-unsaturated uridine with NBS in the presence of pivalic acid followed by TMS-cyanide and stannic chloride. Antineoplastic and antiviral activities of those compounds are also discussed.

  DOI：

  10.1080/07328319608002386
• 作为产物：
  描述：

  1'-cyano-2'-deoxy-2'β-bromouridine 在 ammonium cerium(IV) nitrate 、 碘 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以33%的产率得到1-(2-bromo-1-C-cyano-2-deoxy-3,5-di-O-t-butyldimethylsilyl-β-D-arabino-pentofuranosyl)-5-iodouracil
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 1′-C-Cyano-Pyrimidine Nucleosides

  摘要：

  2'-Deoxy-, 2'-bromo-, and arabine-1'-C-cyano-pyrimidine nucleosides were synthesized from O-2,2'-cyclouridine. Incorporation of cyano group at the anomeric position was achieved by treatment of 1',2'-unsaturated uridine with NBS in the presence of pivalic acid followed by TMS-cyanide and stannic chloride. Antineoplastic and antiviral activities of those compounds are also discussed.

  DOI：

  10.1080/07328319608002386