5'-dimethylamino-5'-deoxy-2',3'-bis(tert-butyldimethylsilyl)adenosine | 249550-82-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 5'-dimethylamino-5'-deoxy-2',3'-bis(tert-butyldimethylsilyl)adenosine
• CAS: 249550-82-1
• 化学式: C₂₄H₄₆N₆O₃Si₂
• 分子量: 522.839
• InChiKey: APZSKQURIFQPNK-WGQQHEPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  100.55
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5'-dimethylamino-5'-deoxy-2',3'-bis(tert-butyldimethylsilyl)adenosine 在 三氟化硼乙醚 、 乙硫醇 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.0h， 生成 N-(5'-adenosyl)-N-[(3S)-3-amino-3-carboxypropyl]-N,N-dimethylammonium iodide
  参考文献：
  名称：

  Synthesis of Two Stable Nitrogen Analogues of S-Adenosyl-l-methionine

  摘要：

  Homochiral syntheses of two stable nitrogen analogues of S-adenosyl-L-methionine (AdoMet) are described. In the first analogue, AzaAdoMet, the sulfonium center of AdoMet, is replaced by an N-methyl moiety whose pK(a) is 7.08. This provides a charge-switchable analogue of AdoMet whose ionic state is a function of the pH. A second analogue, MeAzaAdoMet, has a quaternary dimethylammonium group in place of the methylsulfonium center of AdoMet: thus, its ionic state is independent of pH.

  DOI：

  10.1021/jo9907742
• 作为产物：
  描述：

  2',3'-O,O-bis(t-butyldimethylsilyl)adenosine 在 吡啶 作用下， 反应 144.0h， 生成 5'-dimethylamino-5'-deoxy-2',3'-bis(tert-butyldimethylsilyl)adenosine
  参考文献：
  名称：

  Synthesis of Two Stable Nitrogen Analogues of S-Adenosyl-l-methionine

  摘要：

  Homochiral syntheses of two stable nitrogen analogues of S-adenosyl-L-methionine (AdoMet) are described. In the first analogue, AzaAdoMet, the sulfonium center of AdoMet, is replaced by an N-methyl moiety whose pK(a) is 7.08. This provides a charge-switchable analogue of AdoMet whose ionic state is a function of the pH. A second analogue, MeAzaAdoMet, has a quaternary dimethylammonium group in place of the methylsulfonium center of AdoMet: thus, its ionic state is independent of pH.

  DOI：

  10.1021/jo9907742