(1R,2S,3R,4S)-6-chloro-9-[2,3,4-tris-(tert-butyldimethylsilanyloxy)cyclopentyl]-9H-purine | 865719-97-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (1R,2S,3R,4S)-6-chloro-9-[2,3,4-tris-(tert-butyldimethylsilanyloxy)cyclopentyl]-9H-purine
• 英文别名: [(1S,2R,3S,4R)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-4-(6-chloropurin-9-yl)cyclopentyl]oxy-tert-butyl-dimethylsilane
• CAS: 865719-97-7
• 化学式: C₂₈H₅₃ClN₄O₃Si₃
• 分子量: 613.463
• InChiKey: REOUOHAJCKVBIR-DWQJTFDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4S)-6-chloro-9-[2,3,4-tris-(tert-butyldimethylsilanyloxy)cyclopentyl]-9H-purine 在 正丁基锂 、 氟化铵 、 氨 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 98.5h， 生成 (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：

  叔丁基二甲基氯硅烷 、 (1S,2S,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(6-chloropurin-9-yl)cyclopentane-1,2-diol 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以95%的产率得到(1R,2S,3R,4S)-6-chloro-9-[2,3,4-tris-(tert-butyldimethylsilanyloxy)cyclopentyl]-9H-purine
  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