1-N-benzyl-2',3',5'-tri-O-acetyladenosine | 866325-38-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 1-N-benzyl-2',3',5'-tri-O-acetyladenosine
• 英文别名: 2',3',5'-tri-O-acetyl-1-benzyladenosine；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(1-benzyl-6-iminopurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 866325-38-4
• 化学式: C₂₃H₂₅N₅O₇
• 分子量: 483.481
• InChiKey: MKSYMRNANPRUJP-ZDXOVATRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-N-benzyl-2',3',5'-tri-O-acetyladenosine 在 氨 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 4.25h， 以53%的产率得到1-N-benzyladenosine chlorohydrate
  参考文献：
  名称：

  Regioselective 1-N-Alkylation and Rearrangement of Adenosine Derivatives

  摘要：

  Several methods for the preparation of some N-6-substituted adenosines based on selective 1-N-alkylation with subsequent Dimroth rearrangement were developed. The proposed methods seem to be effective for the preparation of natural N-6-isopentenyl- and N-6-benzyladenosines, which are known to possess pronounced biological activities. Direct 1-N-alkylation of 2 ',3 ',5 '-tri-O-acetyladenosine and 3 ',5 '-di-O-acetyl-2 '-deoxyadenosine with alkyl halides in N,N-dimethylformamide (DMF) in the presence of BaCO3 and KI gave 1-N-substituted derivatives with quantitative yields, whereas 1-N-alkylation of adenosine was accompanied by significant O-alkylation. Moreover, the reaction of trimethylsilyl derivatives of N-6-acetyl-2 ',3 ',5 '-tri-O-acetyladenosine and N-6-acetyl-3 ',5 '-di-O-acetyl-2 '-deoxyadenosine with alkyl halides leads to the formation of the stable 1-N-substituted adenosines. Dimroth rearrangement of 1-N-substituted adenosines in aqueous ammonia yields pure N-6-substituted adenosines.

  DOI：

  10.1080/15257770.2015.1016169
• 作为产物：
  描述：

  2’,3’,5’-三乙酰肌苷 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 1-N-benzyl-2',3',5'-tri-O-acetyladenosine
  参考文献：
  名称：

  A novel nucleophilic approach to 1-alkyladenosines. A two-step synthesis of [1-15N]adenosine from inosine

  摘要：

  1-(2,4-二硝基苯磺酰基)肌苷与胺反应中的一种新颖的 ANRORC 机制，使得能够从肌苷直接制备1-烷基腺苷和[1-15N]腺苷。

  DOI：

  10.1039/b505183e