[6-13C,1,3,4-15N3]-N⁴-benzoylcytosine | 503015-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [6-13C,1,3,4-15N3]-N⁴-benzoylcytosine
• 英文别名: N-(2-oxo-(413C,1,3-15N2)1H-pyrimidin-6-yl)(15N)benzamide
• CAS: 503015-35-8
• 化学式: C₁₁H₉N₃O₂
• 分子量: 219.18
• InChiKey: XBDUZBHKKUFFRH-JAJRULOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4,6-penta-O-acetyl-D-(13C6)glucopyranose 、 [6-13C,1,3,4-15N3]-N⁴-benzoylcytosine 在 苯磺酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 以87.5%的产率得到[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[4-(benzoyl(15N)amino)-2-oxo(613C,1,3-15N2)pyrimidin-1-yl](2,3,4,5,6-13C5)oxan-2-yl](113C)methyl acetate
  参考文献：
  名称：

  A Short Path Synthesis of [¹³C/¹⁵N] Multilabeled Pyrimidine Nucleosides Starting from Glucopyranose Nucleosides

  摘要：

  The synthesis of fully [C-13/N-15] labeled pyrimidine nucleosides has been achieved from C-13-glucose and labeled nucleobases. The reaction scheme leads directly to the protected nucleosides without the need for the inversion of configuration of C-3 of C-13-glucose. This was achieved by an oxitative ring-opening reaction removing the carbon with the wrong configuration.

  DOI：

  10.1021/jo0205098
• 作为产物：
  描述：

  苯甲酰氯 、 [6-13C,1,3,4-15N3]-cytosine 在 吡啶 作用下， 反应 6.0h， 以76%的产率得到[6-13C,1,3,4-15N3]-N⁴-benzoylcytosine
  参考文献：
  名称：

  A Short Path Synthesis of [¹³C/¹⁵N] Multilabeled Pyrimidine Nucleosides Starting from Glucopyranose Nucleosides

  摘要：

  The synthesis of fully [C-13/N-15] labeled pyrimidine nucleosides has been achieved from C-13-glucose and labeled nucleobases. The reaction scheme leads directly to the protected nucleosides without the need for the inversion of configuration of C-3 of C-13-glucose. This was achieved by an oxitative ring-opening reaction removing the carbon with the wrong configuration.

  DOI：

  10.1021/jo0205098

文献信息

• A Short Path Synthesis of [¹³C/¹⁵N] Multilabeled Pyrimidine Nucleosides Starting from Glucopyranose Nucleosides
  作者：Irene M. Lagoja、Sylvie Pochet、Valerie Boudou、Roy Little、Eveline Lescrinier、Jef Rozenski、Piet Herdewijn

  DOI：10.1021/jo0205098

  日期：2003.3.1

  The synthesis of fully [C-13/N-15] labeled pyrimidine nucleosides has been achieved from C-13-glucose and labeled nucleobases. The reaction scheme leads directly to the protected nucleosides without the need for the inversion of configuration of C-3 of C-13-glucose. This was achieved by an oxitative ring-opening reaction removing the carbon with the wrong configuration.