1-((2R,3R,4S)-4-(4-methoxybenzyloxy)-tetrahydro-3-hydroxyfuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione | 1333503-58-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((2R,3R,4S)-4-(4-methoxybenzyloxy)-tetrahydro-3-hydroxyfuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS: 1333503-58-4
• 化学式: C₁₇H₂₀N₂O₆
• 分子量: 348.356
• InChiKey: LPGOFLODXMGAJS-SQWLQELKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.33
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  102.78
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-((2R,3R,4S)-4-(4-methoxybenzyloxy)-tetrahydro-3-hydroxyfuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 在 4-二甲氨基吡啶 、 ammonium cerium (IV) nitrate 、 对甲苯基氯化亚硫代甲酸 、 水 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 1-(2′-deoxy-α-L-threofuranosyl)thymine
  参考文献：
  名称：

  Synthesis and antiviral evaluation of α-l-2′-deoxythreofuranosyl nucleosides

  摘要：

  The synthesis of a series of alpha-L-2'-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-alpha-L-threose, involving a Vorbruggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleoside phosphate prodrug of the T analogue, were evaluated against a broad panel of different viruses but found inactive, while also lacking notable cellular toxicity. The thymidine analogue showed inhibition to mitochondrial thymidine kinase-2 (TK-2), herpes simplex virus type 1 (HSV-1) TK, varicella-zoster virus (VZV) TK and Mycobacterium tuberculosis thymidylate kinase. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.036
• 作为产物：
  描述：

  (2R,3R,4S)-4-(4-methoxybenzyloxy)-tetrahydro-2-(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)furan-3-yl acetate 在 甲醇 、 氨 作用下， 反应 6.0h， 以78%的产率得到1-((2R,3R,4S)-4-(4-methoxybenzyloxy)-tetrahydro-3-hydroxyfuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and antiviral evaluation of α-l-2′-deoxythreofuranosyl nucleosides

  摘要：

  The synthesis of a series of alpha-L-2'-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-alpha-L-threose, involving a Vorbruggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleoside phosphate prodrug of the T analogue, were evaluated against a broad panel of different viruses but found inactive, while also lacking notable cellular toxicity. The thymidine analogue showed inhibition to mitochondrial thymidine kinase-2 (TK-2), herpes simplex virus type 1 (HSV-1) TK, varicella-zoster virus (VZV) TK and Mycobacterium tuberculosis thymidylate kinase. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.036