8-bromo-9-(2-deoxy-2-fluoro-3,5-di-O-tetrahydropyran-2-yl-β-D-ribofuranosyl)adenine | 259144-92-8

• 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-3,5-di-O-tetrahydropyran-2-yl-β-D-ribofuranosyl)adenine
• 英文别名: 8-bromo-9-[(2R,3R,4R,5R)-3-fluoro-4-(oxan-2-yloxy)-5-(oxan-2-yloxymethyl)oxolan-2-yl]purin-6-amine
• CAS: 259144-92-8
• 化学式: C₂₀H₂₇BrFN₅O₅
• 分子量: 516.367
• InChiKey: JANWEKQTQTYSKC-TUHRXIORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  115.77
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  8-bromo-9-(2-deoxy-2-fluoro-3,5-di-O-tetrahydropyran-2-yl-β-D-ribofuranosyl)adenine 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 以76%的产率得到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
• 作为产物：
  描述：

  8-bromo-9-(2-O-acetyl-β-D-arabinofuranosyl)adenine 在 lithium aluminium tetrahydride 、 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 、 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-3,5-di-O-tetrahydropyran-2-yl-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