(1R,2S,3R,4S)-8-benzenesulfonyl-9-[2,3,4-tris-(tert-butyldimethylsilanyloxy)cyclopentyl]-9H-purin-6-ylamine | 865720-00-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1R,2S,3R,4S)-8-benzenesulfonyl-9-[2,3,4-tris-(tert-butyldimethylsilanyloxy)cyclopentyl]-9H-purin-6-ylamine
• CAS: 865720-00-9
• 化学式: C₃₄H₅₉N₅O₅SSi₃
• 分子量: 734.195
• InChiKey: BWOCKXHDZHIWRG-JWNHKAHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.36
• 重原子数：
  48.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  131.45
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4S)-8-benzenesulfonyl-9-[2,3,4-tris-(tert-butyldimethylsilanyloxy)cyclopentyl]-9H-purin-6-ylamine 在 氟化铵 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以76%的产率得到(1R,2S,3R,4S)-4-(6-amino-8-benzenesulfonylpurin-9-yl)cyclopentane-1,2,3-triol
  参考文献：
  名称：

  An Unusual Occurrence on Attempted Purine C-8 Electrophilic Fluorination of 5‘-Noraristeromycin

  摘要：

  Reaction of the in situ generated purine C-8 carbanion of a protected 5'-noraristeromycin derivative with N-fluorobenzenesulfonimide gave 8-phenylsulfonyl-5'-noraristeromycin rather than the expected 8-fluoro derivative. A single electron transfer (SET) mechanism is proposed for this occurrence. The phenylsulfonyl product offers a structural feature common to some anti-HIV agents.

  DOI：

  10.1021/ol051297e
• 作为产物：
  描述：

  (1R,2S,3R,4S)-6-chloro-9-[2,3,4-tris-(tert-butyldimethylsilanyloxy)cyclopentyl]-9H-purine 在 正丁基锂 、 氨 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 26.5h， 生成 (1R,2S,3R,4S)-8-benzenesulfonyl-9-[2,3,4-tris-(tert-butyldimethylsilanyloxy)cyclopentyl]-9H-purin-6-ylamine
  参考文献：
  名称：

  An Unusual Occurrence on Attempted Purine C-8 Electrophilic Fluorination of 5‘-Noraristeromycin

  摘要：

  Reaction of the in situ generated purine C-8 carbanion of a protected 5'-noraristeromycin derivative with N-fluorobenzenesulfonimide gave 8-phenylsulfonyl-5'-noraristeromycin rather than the expected 8-fluoro derivative. A single electron transfer (SET) mechanism is proposed for this occurrence. The phenylsulfonyl product offers a structural feature common to some anti-HIV agents.

  DOI：

  10.1021/ol051297e