8-bromo-9-(2-O-triflyl-3,5-O-tetraisopropyldisiloxane-1,3-diyl-β-D-ribofuranosyl)adenine | 259144-94-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-bromo-9-(2-O-triflyl-3,5-O-tetraisopropyldisiloxane-1,3-diyl-β-D-ribofuranosyl)adenine
• 英文别名: [(6aR,8R,9R,9aR)-8-(6-amino-8-bromopurin-9-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl] trifluoromethanesulfonate
• CAS: 259144-94-0
• 化学式: C₂₃H₃₇BrF₃N₅O₇SSi₂
• 分子量: 720.712
• InChiKey: AIBDSGGIBDCUSJ-QTQZEZTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  42.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  149.91
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  8-bromo-9-(2-O-triflyl-3,5-O-tetraisopropyldisiloxane-1,3-diyl-β-D-ribofuranosyl)adenine 在 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.08h， 生成 8-bromo-9-(2-O-acetyl-3,5-di-O-tetrahydropyran-2-yl-β-D-arabinofuranosyl)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-溴膘苷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.92h， 生成 8-bromo-9-(2-O-triflyl-3,5-O-tetraisopropyldisiloxane-1,3-diyl-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