3'-O,5'-O,N3-tritoluoyl-5-iodo-2'-deoxyuridine | 137100-79-9

• 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'-O,5'-O,N3-tritoluoyl-5-iodo-2'-deoxyuridine
• 英文别名: 3'-O,5'-O,N³-tritoluoyl-5-iodo-2'-deoxyuridine
• CAS: 137100-79-9
• 化学式: C₃₃H₂₉IN₂O₈
• 分子量: 708.506
• InChiKey: LQBNKUQZLKGBKH-UPRLRBBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  44.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  122.9
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3'-O,5'-O,N3-tritoluoyl-5-iodo-2'-deoxyuridine 在 四(三苯基膦)钯 sodium methylate 作用下， 以 甲醇 、 六甲基磷酰三胺 为溶剂， 生成 5-乙烯基-2'-脱氧尿苷
  参考文献：
  名称：

  Synthesis of thymidine from 5-iodo-2′-deoxyuridine

  摘要：

  A simple, high yield synthesis of thymidine from 5-iodo-2'-deoxyuridine is described, using tetramethyltin and tetrakis(triphenylphosphine)palladium(0) in hexamethylphoshoric triamide. Likewise, 5-phenyl- and 5-vinyl-2'-deoxyuridine can be obtained, and through reduction of the latter the 5-ethyl analogue is also at hand.

  DOI：

  10.1016/s0040-4039(00)92180-4
• 作为产物：
  描述：

  碘苷 、 对甲基苯甲酰氯 在 吡啶 、 N,N-二异丙基乙胺 作用下， 反应 3.0h， 以89%的产率得到3'-O,5'-O,N3-tritoluoyl-5-iodo-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis of thymidine from 5-iodo-2′-deoxyuridine

  摘要：

  A simple, high yield synthesis of thymidine from 5-iodo-2'-deoxyuridine is described, using tetramethyltin and tetrakis(triphenylphosphine)palladium(0) in hexamethylphoshoric triamide. Likewise, 5-phenyl- and 5-vinyl-2'-deoxyuridine can be obtained, and through reduction of the latter the 5-ethyl analogue is also at hand.

  DOI：

  10.1016/s0040-4039(00)92180-4

文献信息

• Synthesis and Structure of a Nucleoside with π-Conjugated Nitroxide Spin Label Forming a One-Dimensional Ferromagnetic Chain
  作者：Kausik Das、Maren Pink、Suchada Rajca、Andrzej Rajca

  DOI：10.1021/ja060846o

  日期：2006.4.1

  Spin labeled 2'-deoxyuridine, in which a significant fraction of the spin density is delocalized from a nitroxide radical to the DNA base residue, was prepared as a crystalline solid, stable at ambient conditions. The crystal packing, which includes multiple hydrogen bonds, leads to one-dimensional chains of molecules with predominant intrachain ferromagnetic coupling and weaker interchain antiferromagnetic

  自旋标记的 2'-脱氧尿苷，其中很大一部分自旋密度从氮氧自由基离域到 DNA 碱基残基，制备为结晶固体，在环境条件下稳定。包括多个氢键的晶体堆积导致具有主要链内铁磁耦合和较弱链间反铁磁耦合的一维分子链。