8-bromo-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)adenine | 259144-97-3

• 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: 8-bromo-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)adenine
• 英文别名: (2R,3R,4R,5R)-5-(6-amino-8-bromopurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol
• CAS: 259144-97-3
• 化学式: C₁₀H₁₁BrFN₅O₃
• 分子量: 348.131
• InChiKey: JRKCOVPSUABUJW-DXTOWSMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.24
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  119.31
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 8-bromo-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)adenine 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 以81%的产率得到N6,O3',O5'-triacetyl-2'-deoxy-2'-fluoro-8-oxoadenosine
  参考文献：
  名称：

  Synthesis of 8-Substituted Analogues of 2′-Deoxy-2′-Fluoroadenosine

  摘要：

  After 3',5'-di-O-protection of 8-bromoadenosine, the product was converted to the arabinoside, which was successively treated with diethylaminosulfur trifluoride (DAST) and acid to afford 8-bromo-2'-deoxy-2'-fluoroadenosine. However, the formation of an 8,2'-anhydro compound was noted by treatment of the arabinoside with alkali. Finally, the 8-oxo analog was obtained from the 8-bromo congener.

  DOI：

  10.1080/07328319908044618
• 作为产物：
  描述：

  8-bromo-9-(2-O-acetyl-β-D-arabinofuranosyl)adenine 在 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.08h， 生成 8-bromo-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)adenine
  参考文献：
  名称：

  Synthesis of 8-Substituted Analogues of 2′-Deoxy-2′-Fluoroadenosine

  摘要：

  After 3',5'-di-O-protection of 8-bromoadenosine, the product was converted to the arabinoside, which was successively treated with diethylaminosulfur trifluoride (DAST) and acid to afford 8-bromo-2'-deoxy-2'-fluoroadenosine. However, the formation of an 8,2'-anhydro compound was noted by treatment of the arabinoside with alkali. Finally, the 8-oxo analog was obtained from the 8-bromo congener.

  DOI：

  10.1080/07328319908044618