8-azido-5'-aziridino-5'-deoxy-2',3'-bis(O-tert-butyldimethylsilyl)adenosine | 671792-96-4

• 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: 8-azido-5'-aziridino-5'-deoxy-2',3'-bis(O-tert-butyldimethylsilyl)adenosine
• CAS: 671792-96-4
• 化学式: C₂₄H₄₃N₉O₃Si₂
• 分子量: 561.835
• InChiKey: MXMFJDCJRNMNJJ-QTQZEZTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.34
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  149.08
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  8-azido-5'-aziridino-5'-deoxy-2',3'-bis(O-tert-butyldimethylsilyl)adenosine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以60%的产率得到8-azido-5'-aziridino-5'-deoxy-adenosine
  参考文献：
  名称：

  Efficient Synthesis of Azide-Bearing Cofactor Mimics

  摘要：

  8-Azido-5'-aziridino-5'-deoxyadenosine (6), a novel cofactor mimic, was synthesized in nine steps from commercially available 2',3'-isopropylideneadenosine in similar to4% overall yield. Crucial to this success was a very unorthodox phthalimide cleavage procedure, C8 azidation prior to aziridination and late stage alkylation of the 5' amino group with iodoethanol necessitated by the high degree of lability endowed by the aryl azide moiety. Aziridine 6 is envisioned as a useful biochemical tool by which to probe DNA and protein methylation patterns.

  DOI：

  10.1021/jo035485z
• 作为产物：
  描述：

  2-(((3aR,4R,6R,6aR)-6-(6-氨基-9H-嘌呤-9-基)-2,2-二甲基四氢呋喃并[3,4-d][1,3]二氧代-4-基)甲基)异吲哚啉-1,3-二酮 在 咪唑 、 sodium azide 、 溴 、 sodium acetate 、 乙二胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 32.5h， 生成 8-azido-5'-aziridino-5'-deoxy-2',3'-bis(O-tert-butyldimethylsilyl)adenosine
  参考文献：
  名称：

  Efficient Synthesis of Azide-Bearing Cofactor Mimics

  摘要：

  8-Azido-5'-aziridino-5'-deoxyadenosine (6), a novel cofactor mimic, was synthesized in nine steps from commercially available 2',3'-isopropylideneadenosine in similar to4% overall yield. Crucial to this success was a very unorthodox phthalimide cleavage procedure, C8 azidation prior to aziridination and late stage alkylation of the 5' amino group with iodoethanol necessitated by the high degree of lability endowed by the aryl azide moiety. Aziridine 6 is envisioned as a useful biochemical tool by which to probe DNA and protein methylation patterns.

  DOI：

  10.1021/jo035485z