1-[2',3',5'-tris(O-tert.-butyldimethylsilyl)-β-D-ribofuranosyl]-(1,2,4-triazol-3-yl)-carboxaldehyde | 943984-44-9

• 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: 1-[2',3',5'-tris(O-tert.-butyldimethylsilyl)-β-D-ribofuranosyl]-(1,2,4-triazol-3-yl)-carboxaldehyde
• 英文别名: 1-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-1,2,4-triazole-3-carbaldehyde
• CAS: 943984-44-9
• 化学式: C₂₆H₅₃N₃O₅Si₃
• 分子量: 571.98
• InChiKey: CWXZREWQYUZZSN-JMJGKCIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.79
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[2',3',5'-tris(O-tert.-butyldimethylsilyl)-β-D-ribofuranosyl]-(1,2,4-triazol-3-yl)-carboxaldehyde 在 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-(2',3',5'-tris-(O-tert-butyldimethylsilyl)-1-β-D-ribofuranosyl-[1,2,4]triazole-3-yl)-ethanone
  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：

  三乙酰利巴韦林甲酯 在 咪唑 、 4-二甲氨基吡啶 、 sodium methylate 、 二异丁基氢化铝 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1-[2',3',5'-tris(O-tert.-butyldimethylsilyl)-β-D-ribofuranosyl]-(1,2,4-triazol-3-yl)-carboxaldehyde
  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

文献信息

• [EN] AZOLE NUCLEOSIDES AND USE AS INHIBITORS OF RNA AND DNA VARIAL POLYMERASES<br/>[FR] NUCLEOSIDES D'AZOLE ET UTILISATION EN TANT QU'INHIBITEURS DE POLYMERASES D'ARN ET D'ADN VIRAL
  申请人：SOUTHERN RES INST

  公开号：WO2008067002A3

  公开（公告）日：2008-11-06
• Structural effects on the phosphorylation of 3-substituted 1-β-d-ribofuranosyl-1,2,4-triazoles by human adenosine kinase
  作者：Sidath C. Kumarapperuma、Yanjie Sun、Marjan Jeselnik、Kiwon Chung、William B. Parker、Colleen B. Jonsson、Jeffrey B. Arterburn

  DOI：10.1016/j.bmcl.2007.03.018

  日期：2007.6

  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.