3'-azido-3'-deoxy-4'-hydroxymethylribocytidine | 153914-92-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3'-azido-3'-deoxy-4'-hydroxymethylribocytidine
• 英文别名: 4-amino-1-[(2R,3R,4S)-4-azido-3-hydroxy-5,5-bis(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 153914-92-2
• 化学式: C₁₀H₁₄N₆O₅
• 分子量: 298.258
• InChiKey: LEDCQGVANFQWPV-GJMOJQLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3'-azido-3'-deoxy-4'-hydroxymethylribocytidine 在 ammonium hydroxide 、 三苯基膦 作用下， 生成 3'-amino-3'-deoxy-4'-hydroxymethylribocytidine
  参考文献：
  名称：

  Novel 4′-Branched Nucleosides

  摘要：

  Total chemical synthesis of 4'-hydroxymethylnucleosides with an additional modification in a sugar residue was developed. The synthesis was made by condensation of corresponding protected sugars and nucleic bases with subsequent deprotection. In such a way 3'-azido- and 3'-amino-3'deoxy-4'-hydroxymethylribonucleosides, 2',3'-anhydroribo- and 2',3'-anhydrolyxo-4'-hydroxymethylribonucleosides as well as 3'-deoxy-4'hydroxymethylribollucleosides were prepared. At concentrations up to 100 mu M none of them inhibited reproduction of human immunodeficiency virus type 1 in H9 and PBL cells as well as human herpes simplex virus type 2 and human cytomegalovirus in vero cells.

  DOI：

  10.1080/15257779408013221
• 作为产物：
  描述：

  1,2-di-O-acetyl-3-azido-5-O-benzoyl-4-benzoyloxymethyl-3-deoxy-β-D-ribofuranose 在 四氯化硅 、 氨 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 3'-azido-3'-deoxy-4'-hydroxymethylribocytidine
  参考文献：
  名称：

  Novel 4′-Branched Nucleosides

  摘要：

  Total chemical synthesis of 4'-hydroxymethylnucleosides with an additional modification in a sugar residue was developed. The synthesis was made by condensation of corresponding protected sugars and nucleic bases with subsequent deprotection. In such a way 3'-azido- and 3'-amino-3'deoxy-4'-hydroxymethylribonucleosides, 2',3'-anhydroribo- and 2',3'-anhydrolyxo-4'-hydroxymethylribonucleosides as well as 3'-deoxy-4'hydroxymethylribollucleosides were prepared. At concentrations up to 100 mu M none of them inhibited reproduction of human immunodeficiency virus type 1 in H9 and PBL cells as well as human herpes simplex virus type 2 and human cytomegalovirus in vero cells.

  DOI：

  10.1080/15257779408013221

文献信息

• Surzhikov, S. A.; Dyatkina, N. B., Russian Journal of Bioorganic Chemistry, 1993, vol. 19, # 7, p. 408 - 413
  作者：Surzhikov, S. A.、Dyatkina, N. B.

  DOI：——

  日期：——
• Novel 4′-Branched Nucleosides
  作者：S. A. Surzhykov、A. A. Krayevsky

  DOI：10.1080/15257779408013221

  日期：1994.12

  Total chemical synthesis of 4'-hydroxymethylnucleosides with an additional modification in a sugar residue was developed. The synthesis was made by condensation of corresponding protected sugars and nucleic bases with subsequent deprotection. In such a way 3'-azido- and 3'-amino-3'deoxy-4'-hydroxymethylribonucleosides, 2',3'-anhydroribo- and 2',3'-anhydrolyxo-4'-hydroxymethylribonucleosides as well as 3'-deoxy-4'hydroxymethylribollucleosides were prepared. At concentrations up to 100 mu M none of them inhibited reproduction of human immunodeficiency virus type 1 in H9 and PBL cells as well as human herpes simplex virus type 2 and human cytomegalovirus in vero cells.