[(2R,3S,5R)-3-acetyloxy-5-[5-(3-methyl-1,2-oxazol-5-yl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate | 1138334-76-5

• 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,3S,5R)-3-acetyloxy-5-[5-(3-methyl-1,2-oxazol-5-yl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate
• CAS: 1138334-76-5
• 化学式: C₁₇H₁₉N₃O₈
• 分子量: 393.353
• InChiKey: PWZULBCHWPUIPZ-RRFJBIMHSA-N

物化性质

• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-3-acetyloxy-5-[5-(3-methyl-1,2-oxazol-5-yl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 生成 5-(3-methylisoxazol-5-yl)-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis of 5-isoxazol-5-yl-2′-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses

  摘要：

  This paper describes a simple method for synthesizing a small library of 5-isoxazol-5-yl-2 '-deoxyuridines from 5-iodo-2 '-deoxyuridine. Nitrile oxides were generated in situ from oximes using a commercial bleaching agent; their cycloaddition with 5-ethynyl-2 '-deoxyuridine yielded isoxazoles possessing activity against herpes simplex viruses 1 and 2, Encephalomyocarditis virus, Coxsackie B3, and vesicular stomatitis virus; these isoxazoles were, however, inactive against corona virus, influenza virus, and HIV. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.12.103
• 作为产物：
  描述：

  乙醛肟 、 5-ethynyl-2'-deoxyuridine 在 sodium hypochlorite 作用下， 以 四氢呋喃 为溶剂， 生成 [(2R,3S,5R)-3-acetyloxy-5-[5-(3-methyl-1,2-oxazol-5-yl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of 5-isoxazol-5-yl-2′-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses

  摘要：

  This paper describes a simple method for synthesizing a small library of 5-isoxazol-5-yl-2 '-deoxyuridines from 5-iodo-2 '-deoxyuridine. Nitrile oxides were generated in situ from oximes using a commercial bleaching agent; their cycloaddition with 5-ethynyl-2 '-deoxyuridine yielded isoxazoles possessing activity against herpes simplex viruses 1 and 2, Encephalomyocarditis virus, Coxsackie B3, and vesicular stomatitis virus; these isoxazoles were, however, inactive against corona virus, influenza virus, and HIV. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.12.103