(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(3-amino-1H-1,2,4-triazol-1-yl)tetrahydrofuran-3,4-diyl diacetate | 943984-47-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 三唑核糖核苷和核糖核苷酸
• 英文名称: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(3-amino-1H-1,2,4-triazol-1-yl)tetrahydrofuran-3,4-diyl diacetate
• CAS: 943984-47-2
• 化学式: C₁₃H₁₈N₄O₇
• 分子量: 342.309
• InChiKey: KEWSKABAZQRSCZ-DDHJBXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.82
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  144.86
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(3-amino-1H-1,2,4-triazol-1-yl)tetrahydrofuran-3,4-diyl diacetate 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 4.0h， 生成 N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazol-3-yl]acetamide
  参考文献：
  名称：

  Structural effects on the phosphorylation of 3-substituted 1-β-d-ribofuranosyl-1,2,4-triazoles by human adenosine kinase

  摘要：

  The conversion of ribavirin to the monophosphate by adenosine kinase is the rate-limiting step in activation of this broad spectrum antiviral drug. Variation of the 3-substituents in a series of bioisosteric and homologated 1-beta-D-ribofuranosyl-1,2,4-triazoles has marked effects on activity with the human adenosine kinase, and analysis of computational descriptors and binding models offers insight for the design of novel substrates. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.018
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 在 4-二甲氨基吡啶 、 三乙胺 、 肼 作用下， 以 水 、 乙腈 为溶剂， 反应 16.5h， 生成 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(3-amino-1H-1,2,4-triazol-1-yl)tetrahydrofuran-3,4-diyl diacetate
  参考文献：
  名称：

  Structural effects on the phosphorylation of 3-substituted 1-β-d-ribofuranosyl-1,2,4-triazoles by human adenosine kinase

  摘要：

  The conversion of ribavirin to the monophosphate by adenosine kinase is the rate-limiting step in activation of this broad spectrum antiviral drug. Variation of the 3-substituents in a series of bioisosteric and homologated 1-beta-D-ribofuranosyl-1,2,4-triazoles has marked effects on activity with the human adenosine kinase, and analysis of computational descriptors and binding models offers insight for the design of novel substrates. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.018