(5'R)-<5'-(2)H>-N⁴-Benzoyl-2'-deoxycytidine | 154976-33-7

• 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: (5'R)-<5'-(2)H>-N⁴-Benzoyl-2'-deoxycytidine
• 英文别名: N-[1-[(2R,4S,5R)-5-[(R)-deuterio(hydroxy)methyl]-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 154976-33-7
• 化学式: C₁₆H₁₇N₃O₅
• 分子量: 332.32
• InChiKey: MPSJHJFNKMUKCN-GDOLMDNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5'R)-<5'-(2)H>-N⁴-Benzoyl-2'-deoxycytidine 在 Dowex 50W acid resin (pyridinium form) 、 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 5.2h， 生成 (5'S)-<5'-(2)H>-N⁴-Benzoyl-2'-deoxycytidine
  参考文献：
  名称：

  General Approach to the Synthesis of Specifically Deuterium-Labeled Nucleosides

  摘要：

  Starting from D-(-)-ribose, a set of synthetic routes sharing common intermediates has been developed and exemplified in [5'-H-2(2)]-, [4'-H-2]-, [1'-H-2]-, (5'R)-[5'-H-2]-, and (5'S)-[5'-H-2]-N-4-benzoylcytidine and, by deoxygenation, their corresponding 2'-deoxynucleosides. These syntheses provide convenient access to millimolar quantities of deuterium/tritium-labeled natural or unnatural nucleosides for direct use or automated oligonucleotide synthesis.

  DOI：

  10.1021/jo00089a013
• 作为产物：
  描述：

  N4-苯甲酰基胞嘧啶 在 苯磺酰胺 、 四氯化锡 、 三氟乙酸 作用下， 反应 4.83h， 生成 (5'R)-<5'-(2)H>-N⁴-Benzoyl-2'-deoxycytidine
  参考文献：
  名称：

  General Approach to the Synthesis of Specifically Deuterium-Labeled Nucleosides

  摘要：

  Starting from D-(-)-ribose, a set of synthetic routes sharing common intermediates has been developed and exemplified in [5'-H-2(2)]-, [4'-H-2]-, [1'-H-2]-, (5'R)-[5'-H-2]-, and (5'S)-[5'-H-2]-N-4-benzoylcytidine and, by deoxygenation, their corresponding 2'-deoxynucleosides. These syntheses provide convenient access to millimolar quantities of deuterium/tritium-labeled natural or unnatural nucleosides for direct use or automated oligonucleotide synthesis.

  DOI：

  10.1021/jo00089a013

文献信息

• Specific abstraction of the 5'S- and 4'-deoxyribosyl hydrogen atoms from DNA by calicheamicin .gamma.1I
  作者：Jon J. Hangeland、James J. De Voss、Julie A. Heath、Craig A. Townsend、Wei Dong Ding、Joseph S. Ashcroft、George A. Ellestad

  DOI：10.1021/ja00049a069

  日期：1992.11
• General Approach to the Synthesis of Specifically Deuterium-Labeled Nucleosides
  作者：James J. De Voss、Jon J. Hangeland、Craig A. Townsend

  DOI：10.1021/jo00089a013

  日期：1994.5

  Starting from D-(-)-ribose, a set of synthetic routes sharing common intermediates has been developed and exemplified in [5'-H-2(2)]-, [4'-H-2]-, [1'-H-2]-, (5'R)-[5'-H-2]-, and (5'S)-[5'-H-2]-N-4-benzoylcytidine and, by deoxygenation, their corresponding 2'-deoxynucleosides. These syntheses provide convenient access to millimolar quantities of deuterium/tritium-labeled natural or unnatural nucleosides for direct use or automated oligonucleotide synthesis.