[(2R,3R,4R,5R)-4-benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-2-(1,3,2-oxathiaphospholan-2-yloxymethyl)oxolan-3-yl] benzoate | 1054647-48-1

• 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: [(2R,3R,4R,5R)-4-benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-2-(1,3,2-oxathiaphospholan-2-yloxymethyl)oxolan-3-yl] benzoate
• CAS: 1054647-48-1
• 化学式: C₂₅H₂₃N₂O₉PS
• 分子量: 558.505
• InChiKey: MGXGHBUUGYJUGM-HUZDANFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  155
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-4-benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-2-(1,3,2-oxathiaphospholan-2-yloxymethyl)oxolan-3-yl] benzoate 在 ammonium hydroxide 、 dimethyl sulfide borane 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二丁基丁烷-1-胺,磷酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 uridine 5'-P^α-boranodiphosphate bisammonium salt
  参考文献：
  名称：

  Convenient Synthesis of Nucleoside Borane Diphosphate Analogues:  Deoxy- and Ribonucleoside 5‘-P^α-Boranodiphosphates

  摘要：

  The nucleoside boranophosphates, having one of the nonbridging phosphate oxygens substituted with a borane (BH3) group, have shown potential therapeutical applications as aptamers, antisense agents, and antiviral prodrugs. An oxathiaphospholane approach, which does not require exocyclic amine protection of the nucleobase, has been successfully developed to efficiently synthesize 5'-P-alpha-boranodiphosphates of 2'-deoxythymidine, adenosine, guanosine, and uridine. The approach involves a key intermediate, the borane complex of nucleoside 5'-O-1,3,2-oxathiaphospholane 16, that undergoes a ring-opening reaction catalyzed by 1,4-diazabicyclo[5.4.0]-undec-7-ene to form the protected nucleoside 5'-P-alpha-boranodiphosphate 18. Treatment of 18 with ammonium hydroxide yielded diastereoisomeric mixtures of nucleoside 5'-P-alpha-boranodiphosphates 5. This oxathiaphospholane approach ensures the availability of nucleoside 5'-P-alpha-boranodiphosphate analogues needed for antiviral drug research.

  DOI：

  10.1021/jo049094b
• 作为产物：
  描述：

  2-氯-1,3,2-氧杂硫杂磷杂环戊烷 、 2',3'-二-O-苯甲酰基尿苷 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 [(2R,3R,4R,5R)-4-benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-2-(1,3,2-oxathiaphospholan-2-yloxymethyl)oxolan-3-yl] benzoate
  参考文献：
  名称：

  Convenient Synthesis of Nucleoside Borane Diphosphate Analogues:  Deoxy- and Ribonucleoside 5‘-P^α-Boranodiphosphates

  摘要：

  The nucleoside boranophosphates, having one of the nonbridging phosphate oxygens substituted with a borane (BH3) group, have shown potential therapeutical applications as aptamers, antisense agents, and antiviral prodrugs. An oxathiaphospholane approach, which does not require exocyclic amine protection of the nucleobase, has been successfully developed to efficiently synthesize 5'-P-alpha-boranodiphosphates of 2'-deoxythymidine, adenosine, guanosine, and uridine. The approach involves a key intermediate, the borane complex of nucleoside 5'-O-1,3,2-oxathiaphospholane 16, that undergoes a ring-opening reaction catalyzed by 1,4-diazabicyclo[5.4.0]-undec-7-ene to form the protected nucleoside 5'-P-alpha-boranodiphosphate 18. Treatment of 18 with ammonium hydroxide yielded diastereoisomeric mixtures of nucleoside 5'-P-alpha-boranodiphosphates 5. This oxathiaphospholane approach ensures the availability of nucleoside 5'-P-alpha-boranodiphosphate analogues needed for antiviral drug research.

  DOI：

  10.1021/jo049094b

文献信息

• Convenient Synthesis of Nucleoside Borane Diphosphate Analogues:  Deoxy- and Ribonucleoside 5‘-<i>P</i>^α-Boranodiphosphates
  作者：Ping Li、Barbara Ramsay Shaw

  DOI：10.1021/jo049094b

  日期：2004.10.1

  The nucleoside boranophosphates, having one of the nonbridging phosphate oxygens substituted with a borane (BH3) group, have shown potential therapeutical applications as aptamers, antisense agents, and antiviral prodrugs. An oxathiaphospholane approach, which does not require exocyclic amine protection of the nucleobase, has been successfully developed to efficiently synthesize 5'-P-alpha-boranodiphosphates of 2'-deoxythymidine, adenosine, guanosine, and uridine. The approach involves a key intermediate, the borane complex of nucleoside 5'-O-1,3,2-oxathiaphospholane 16, that undergoes a ring-opening reaction catalyzed by 1,4-diazabicyclo[5.4.0]-undec-7-ene to form the protected nucleoside 5'-P-alpha-boranodiphosphate 18. Treatment of 18 with ammonium hydroxide yielded diastereoisomeric mixtures of nucleoside 5'-P-alpha-boranodiphosphates 5. This oxathiaphospholane approach ensures the availability of nucleoside 5'-P-alpha-boranodiphosphate analogues needed for antiviral drug research.