5'-(2''-carboxymethylaziridino)-5'-deoxy-2',3'-bis(O-triethylsilyl)adenosine | 473907-70-9

• 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'-(2''-carboxymethylaziridino)-5'-deoxy-2',3'-bis(O-triethylsilyl)adenosine
• 英文别名: methyl (2R)-1-[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]methyl]aziridine-2-carboxylate
• CAS: 473907-70-9
• 化学式: C₂₆H₄₆N₆O₅Si₂
• 分子量: 578.859
• InChiKey: ZQTRXSMEQLIWCM-PSEKCLAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  39.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  126.62
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  5'-(2''-carboxymethylaziridino)-5'-deoxy-2',3'-bis(O-triethylsilyl)adenosine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以66%的产率得到5'-[(2''-hydroxymethyl)aziridino]-5'-deoxy-2',3'-bis(O-triethylsilyl)adenosine
  参考文献：
  名称：

  Expeditious synthesis of aziridine-based cofactor mimics

  摘要：

  S-Adenosyl-L-methionine mimics were synthesized in a linear fashion highlighting methodology that bypasses the need for adenine base protection. These aziridine-based cofactor mimics are envisioned as useful biochemical tools and potential therapeutic agents whose mechanism of action hinges upon aberrant methyltransferase enzymes. Aziridination of the 5' position of adenosine was effected by convergence of suitably protected 5'-aminoadenosine with various dibromopropionates. The economy and high yields for this route to said aziridine-based cofactors is highly amenable to large-scale chemistry which no doubt will be vital to their development as therapeutics and biochemical tools. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00590-2
• 作为产物：
  描述：

  5'-azido-5'-deoxyadenosine 在 咪唑 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 5'-(2''-carboxymethylaziridino)-5'-deoxy-2',3'-bis(O-triethylsilyl)adenosine
  参考文献：
  名称：

  Expeditious synthesis of aziridine-based cofactor mimics

  摘要：

  S-Adenosyl-L-methionine mimics were synthesized in a linear fashion highlighting methodology that bypasses the need for adenine base protection. These aziridine-based cofactor mimics are envisioned as useful biochemical tools and potential therapeutic agents whose mechanism of action hinges upon aberrant methyltransferase enzymes. Aziridination of the 5' position of adenosine was effected by convergence of suitably protected 5'-aminoadenosine with various dibromopropionates. The economy and high yields for this route to said aziridine-based cofactors is highly amenable to large-scale chemistry which no doubt will be vital to their development as therapeutics and biochemical tools. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00590-2