8-azido-5'-aziridino-5'-deoxy-adenosine | 671792-90-8

• 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-adenosine
• 英文别名: 8-Azido-5'-aziridin-1-yl-5'-deoxyadenosine；(2R,3R,4S,5R)-2-(6-amino-8-azidopurin-9-yl)-5-(aziridin-1-ylmethyl)oxolane-3,4-diol
• CAS: 671792-90-8
• 化学式: C₁₂H₁₅N₉O₃
• 分子量: 333.31
• InChiKey: MYBSLCBUSCMAOM-IOSLPCCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 咪唑 、 sodium azide 、 四丁基氟化铵 、 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 36.0h， 生成 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

文献信息

• Efficient Synthesis of Azide-Bearing Cofactor Mimics
  作者：Lindsay R. Comstock、Scott R. Rajski

  DOI：10.1021/jo035485z

  日期：2004.2.1

  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.