9-(2-O-acetyl-3-azido-5-O-benzoyl-4-benzoyloxymethyl-3-deoxy-β-D-ribofuranosyl)uracil | 153915-01-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-(2-O-acetyl-3-azido-5-O-benzoyl-4-benzoyloxymethyl-3-deoxy-β-D-ribofuranosyl)uracil
• CAS: 153915-01-6
• 化学式: C₂₆H₂₃N₅O₉
• 分子量: 549.497
• InChiKey: LPDYYMVLEMKVEU-BHIFYINESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  192.01
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  9-(2-O-acetyl-3-azido-5-O-benzoyl-4-benzoyloxymethyl-3-deoxy-β-D-ribofuranosyl)uracil 在 氨 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以78.4%的产率得到1-[(2R,3R,4S)-4-azido-3-hydroxy-5,5-bis(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
  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：

  3-azido-5-O-benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-3-deoxy-α-D-ribofuranose 在 吡啶 、 甲酸 、 四氯化硅 作用下， 反应 28.0h， 生成 9-(2-O-acetyl-3-azido-5-O-benzoyl-4-benzoyloxymethyl-3-deoxy-β-D-ribofuranosyl)uracil
  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：——