3-N-benzoyl-3',5'-di-O-benzoyl-5-butyl-2'-deoxyuridine | 1037176-18-3

• 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: 3-N-benzoyl-3',5'-di-O-benzoyl-5-butyl-2'-deoxyuridine
• CAS: 1037176-18-3
• 化学式: C₃₄H₃₂N₂O₈
• 分子量: 596.637
• InChiKey: TZSCAADATQJDIA-ZGIBFIJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  122.9
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  1-碘丁烷 、 3-N-benzoyl-3',5'-di-O-benzoyl-5-iodo-2'-deoxyuridine 在 Pd(P(t-Bu)3) 锌 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.5h， 以15%的产率得到3-N-benzoyl-3',5'-di-O-benzoyl-5-butyl-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis of 5-Fluoroalkylated Pyrimidine Nucleosides via Negishi Cross-Coupling

  摘要：

  5-Fluoroalkylated pyrimidine nucleosides (1) have potential as therapeutic agents and molecular imaging agents targeting HSV1-tk suicide gene therapy. Thus, straightforward preparation of 5-fluoroalkylated nucleoside derivatives has been developed. Reported herein are the first examples of Pd-catalyzed Negishi cross-coupling of 3-N-benzoyl-3',5'-di-O-benzoyl-5-iodo-2'-deoxyuridine (2a) and 3-N-benzoyl-3',5'-di-O-benzoyl-5-iodo-2'-deoxy-2'-fluoroarabinouridine (2b) with unactivated CSp(3) fluoroalkylzinc bromides. This paper demonstrates the first synthesis of six 5-fluoroalkyl-2'-deoxypyrimidine nucleoside derivatives with three to five methylene chain lengths (5). Furthermore, this methodology has been extended to create a series of 13 5-alkyl-substituted nucleosides, including the target nucleosides 5 and 5-silyloxypropyl and 5-cyanobutyl derivatives.

  DOI：

  10.1021/jo800444y