3-N-benzoyl-3',5'-di-O-benzoyl-5-(4-ethoxy-4-oxobutyl)-2'-deoxyuridine | 1037176-22-9

• 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-(4-ethoxy-4-oxobutyl)-2'-deoxyuridine
• 英文别名: [(2R,3S,5R)-5-[3-benzoyl-5-(4-ethoxy-4-oxobutyl)-2,4-dioxopyrimidin-1-yl]-3-benzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 1037176-22-9
• 化学式: C₃₆H₃₄N₂O₁₀
• 分子量: 654.673
• InChiKey: BAJOZUUFIDJGLC-FRXPANAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  146
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-溴丁酸乙酯 、 3-N-benzoyl-3',5'-di-O-benzoyl-5-iodo-2'-deoxyuridine 在 Pd(P(t-Bu)3) 碘 、 锌 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.5h， 以39%的产率得到3-N-benzoyl-3',5'-di-O-benzoyl-5-(4-ethoxy-4-oxobutyl)-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

文献信息

• Synthesis of 5-Fluoroalkylated Pyrimidine Nucleosides via Negishi Cross-Coupling
  作者：Ann-Marie Chacko、Wenchao Qu、Hank F. Kung

  DOI：10.1021/jo800444y

  日期：2008.7.1

  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.