N⁴-benzoyl-[1',2',3',4',5',6'-13C6]-(β-D-glucopyranosyl)-(6-13C,1,3,4-15N3)-cytosine | 373366-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N⁴-benzoyl-[1',2',3',4',5',6'-13C6]-(β-D-glucopyranosyl)-(6-13C,1,3,4-15N3)-cytosine
• 英文别名: N-[2-oxo-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxy(113C)methyl)(2,3,4,5,6-13C5)oxan-2-yl](613C,1,3-15N2)pyrimidin-4-yl](15N)benzamide
• CAS: 373366-04-2
• 化学式: C₁₇H₁₉N₃O₇
• 分子量: 387.257
• InChiKey: BMNJBRIJWSQZNK-PJGJFHBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  152
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-甲氧基三苯基氯甲烷 、 N⁴-benzoyl-[1',2',3',4',5',6'-13C6]-(β-D-glucopyranosyl)-(6-13C,1,3,4-15N3)-cytosine 在 吡啶 、 三乙胺 作用下， 反应 18.0h， 以83%的产率得到6'-O-monomethoxytrityl-N⁴-benzoyl-[1',2',3',4',5',6'-13C6]-(β-D-glucopyranosyl)-(6-13C,1,3,4-15N3)-cytosine
  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 、 [1',2',3',4',5',6'-13C6]-(β-D-glucopyranosyl)-(6-13C,1,3,4-15N3)-cytosine 在 三甲基氯硅烷 、 ammonium chloride 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 反应 22.0h， 以90%的产率得到N⁴-benzoyl-[1',2',3',4',5',6'-13C6]-(β-D-glucopyranosyl)-(6-13C,1,3,4-15N3)-cytosine
  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.