[(2R,3S,5R)-3-acetyloxy-5-[5-[3-(4-tert-butylphenyl)-1,2-oxazol-5-yl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate | 1138334-81-2

• 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-(4-tert-butylphenyl)-1,2-oxazol-5-yl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate
• CAS: 1138334-81-2
• 化学式: C₂₆H₂₉N₃O₈
• 分子量: 511.532
• InChiKey: OMGUMHVXIMQZJT-YTFSRNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 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-(4-tert-butylphenyl)-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-(4-tert-butylphenyl)-1,2-oxazol-5-yl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
  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：

  5-ethynyl-2'-deoxyuridine 、 4-tert-butylbenzaldehyde oxime 在 sodium hypochlorite 作用下， 以 四氢呋喃 为溶剂， 生成 [(2R,3S,5R)-3-acetyloxy-5-[5-[3-(4-tert-butylphenyl)-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