(2R,3R,4R,5R)-4-(azidomethyl)-2-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-3-yl acetate | 1239479-19-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: (2R,3R,4R,5R)-4-(azidomethyl)-2-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-3-yl acetate
• CAS: 1239479-19-6
• 化学式: C₃₃H₃₂N₆O₇
• 分子量: 624.653
• InChiKey: RDZIXEQGUPMFSD-WKIOUMQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  166.74
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-4-(azidomethyl)-2-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-3-yl acetate 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以50%的产率得到
  参考文献：
  名称：

  Synthesis and anti-hepatitis C virus (HCV) activity of 3′-C-substituted-methyl pyrimidine and purine nucleosides

  摘要：

  On the basis of potent anti-hepatitis C virus (HCV) activity of 2'-C-hydroxymethyladenosine, 3'-C-substituted-methyl-ribofuranosyl pyrimidine and purine nucleosides were designed and synthesized from D-xylose. Among compounds tested, all adenine analogues, 4a, 4d, and 4g showed significant anti-HCV activity in a replicon-based cell assay irrespective of the substituent (Y = OH, N-3, or F) at the 3'-C-substituted methyl position, among which 4g (Y = N3) was the most potent, but it is also cytotoxic. This study guarantees the 3'-C-substituted-methyl nucleoside serves as a new template for the development of new anti-HCV agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.002
• 作为产物：
  描述：

  N4-苯甲酰基胞嘧啶 、 3-C-azidomethyl-3,5-di-O-benzyl-1,2-di-O-acetyl-D-ribofuranose 在 硫酸氢铵 、 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 以64%的产率得到(2R,3R,4R,5R)-4-(azidomethyl)-2-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-3-yl acetate
  参考文献：
  名称：

  Synthesis and anti-hepatitis C virus (HCV) activity of 3′-C-substituted-methyl pyrimidine and purine nucleosides

  摘要：

  On the basis of potent anti-hepatitis C virus (HCV) activity of 2'-C-hydroxymethyladenosine, 3'-C-substituted-methyl-ribofuranosyl pyrimidine and purine nucleosides were designed and synthesized from D-xylose. Among compounds tested, all adenine analogues, 4a, 4d, and 4g showed significant anti-HCV activity in a replicon-based cell assay irrespective of the substituent (Y = OH, N-3, or F) at the 3'-C-substituted methyl position, among which 4g (Y = N3) was the most potent, but it is also cytotoxic. This study guarantees the 3'-C-substituted-methyl nucleoside serves as a new template for the development of new anti-HCV agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.002