trimethylsilyl N-(7-(trimethylsilyl)-6-((trimethylsilyl)oxy)-7H-purin-2-yl)acetimidate | 134222-17-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: trimethylsilyl N-(7-(trimethylsilyl)-6-((trimethylsilyl)oxy)-7H-purin-2-yl)acetimidate
• CAS: 134222-17-6
• 化学式: C₁₆H₃₁N₅O₂Si₃
• 分子量: 409.711
• InChiKey: LBEIVYQGHZKJCF-UHFFFAOYSA-N

物化性质

• 沸点：
  424.3±55.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  74.42
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  trimethylsilyl N-(7-(trimethylsilyl)-6-((trimethylsilyl)oxy)-7H-purin-2-yl)acetimidate 在 氨 、 四氯化锡 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 46.0h， 生成 7-β-D-ribofuranosylguanine
  参考文献：
  名称：

  A regiocontrolled synthesis of N7- and N9-guanine nucleosides

  摘要：

  DOI：

  10.1021/jo00241a032
• 作为产物：
  描述：

  N-2-乙酰鸟嘌呤 、 六甲基二硅氮烷 在 硫酸氢铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 trimethylsilyl N-(7-(trimethylsilyl)-6-((trimethylsilyl)oxy)-7H-purin-2-yl)acetimidate
  参考文献：
  名称：

  Stereoselective Synthesis of 2'-Deoxy-.beta.-D-threo-pentofuranosyl Nucleosides by the NBS-Promoted Coupling Reaction of Thioglycosides with Silylated Heterocyclic Bases

  摘要：

  The NBS-promoted coupling reaction of phenyl 3,5-O-isopropylidene-2-deoxy-1-thio-alpha-D-threo-pentofuranoside (5e) with silylated pyrimidine bases was found to proceed in a highly stereoselective manner (alpha:beta = 1:24-0:1) to afford 2'-deoxy-beta-D-threo-pentofuranosyl pyrimidine nucleosides in satisfactory yields. The highly stereoselective outcome is thought to result from an in situ anomerization-type mechanism, in which intimate ionic intermediates would be in equilibrium and anomerize to the sterically preferable a form. A subsequent S(N)2 type attack to the intermediate will lead to the beta-nucleosides. By using this method, the synthesis of L-nucleosides, 1-(2-deoxy-beta-L-threo-pentofuranosyl)thymine and cytosine derivatives, was also demonstrated by starting from the L-enantiomer of the thioglycoside. On the other hand, the reaction with purine bases was accompanied by the production of undesirable N-7 regioisomers besides the desired N-9 products. The product distribution of the regioisomers was, however, proved to change with reaction time. For instance, a long reaction period allowed the thermodynamically stable N-9 isomers to be exclusively produced with moderate selectivity (alpha:beta = 1:2-1:4.8). The isolated yields of the 9-beta isomers after purification were acceptable for practical use.

  DOI：

  10.1021/jo00104a020