methyl 2-[[(2S,3S,5R)-3-azido-5-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]-2-dimethoxyphosphorylacetate | 1259875-25-6

• 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: methyl 2-[[(2S,3S,5R)-3-azido-5-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]-2-dimethoxyphosphorylacetate
• CAS: 1259875-25-6
• 化学式: C₂₂H₂₆N₅O₁₀P
• 分子量: 551.45
• InChiKey: GTJZVOXLNDJAJV-OLFWJBSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 2-[[(2S,3S,5R)-3-azido-5-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]-2-dimethoxyphosphorylacetate 在 三甲基溴硅烷 、 三乙基碳酸氢铵缓冲液 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 2-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]-2-[hydroxy-[hydroxy(phosphonooxy)phosphoryl]oxyphosphoryl]acetic acid
  参考文献：
  名称：

  Design and Synthesis of α-Carboxy Phosphononucleosides

  摘要：

  Rhodium catalyzed O-H insertion reactions employing alpha-diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5'-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an alpha-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2.

  DOI：

  10.1021/jo101738e
• 作为产物：
  描述：

  5’-O-(叔丁基二甲基甲硅烷基)胸苷 在 rhodium(II) acetate dimer 、 4-二甲氨基吡啶 、 sodium azide 、 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 3.0h， 生成 methyl 2-[[(2S,3S,5R)-3-azido-5-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]-2-dimethoxyphosphorylacetate
  参考文献：
  名称：

  Design and Synthesis of α-Carboxy Phosphononucleosides

  摘要：

  Rhodium catalyzed O-H insertion reactions employing alpha-diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5'-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an alpha-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2.

  DOI：

  10.1021/jo101738e

文献信息

• Design and Synthesis of α-Carboxy Phosphononucleosides
  作者：Sebastien Debarge、Jan Balzarini、Anita R. Maguire

  DOI：10.1021/jo101738e

  日期：2011.1.7

  Rhodium catalyzed O-H insertion reactions employing alpha-diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5'-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an alpha-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2.