9-(3'-azido-5'-ethynyl-2',3',5',-trideoxy-β-D-ribofuranosyl)guanine | 1226528-21-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-(3'-azido-5'-ethynyl-2',3',5',-trideoxy-β-D-ribofuranosyl)guanine
• 英文别名: 2-amino-9-[(2R,4S,5R)-4-azido-5-prop-2-ynyloxolan-2-yl]-1H-purin-6-one
• CAS: 1226528-21-7
• 化学式: C₁₂H₁₂N₈O₂
• 分子量: 300.28
• InChiKey: IAYFYGBRPQOLDA-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-β-D-ribofuranosyl)-2-isobutyrylguanine 在 甲醇 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 2.5h， 以95%的产率得到9-(3'-azido-5'-ethynyl-2',3',5',-trideoxy-β-D-ribofuranosyl)guanine
  参考文献：
  名称：

  Synthesis and structures of deoxyribonucleoside analogues for triazole-linked DNA (TLDNA)

  摘要：

  Deoxyribonucleoside analogues bearing acetylene group at the pseudo-5'-position and azido group at the pseudo-3'-position have been synthesized by transglycosylation reaction of deoxythymidine analogue with adenine, cytosine, and guanine nucleobases as nucleophiles. The structures of analogues were studied in crystalline state by X-ray crystallography as well as in solution phase by NMR spectroscopy and showed the puckering conformations similar to the natural congeners. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.046