4'-C-[(N⁶-benzoyladenin-9-yl)-methyl]-thymidine | 879015-12-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: 4'-C-[(N⁶-benzoyladenin-9-yl)-methyl]-thymidine
• 英文别名: N-[9-[[(2R,3S,5R)-3-hydroxy-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]purin-6-yl]benzamide
• CAS: 879015-12-0
• 化学式: C₂₃H₂₃N₇O₆
• 分子量: 493.479
• InChiKey: FVASFBUYBNUVMM-NXHTTZLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  172
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4'-C-[(N⁶-benzoyladenin-9-yl)-methyl]-thymidine 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 5'-O-[(4-methoxyphenyl)diphenylmethyl]-4'-C-[(N⁶-benzoyladenin-9-yl)-methyl]-3'-O-(P-β-cyanoethoxy-N,N-diisopropylaminophosphinyl)-thymidine
  参考文献：
  名称：

  Base−Base Interactions in the Minor Groove of Double-Stranded DNA

  摘要：

  A method has been developed for the synthesis of bisheaded nucleosides with thymine and adenine base moieties. We have demonstrated that, when incorporated in oligonucleotides, extrahelical A-T base interactions are possible when the bisheaded nucleosides are positioned in opposite strands of the duplex and are separated from each other by one regular base pair.

  DOI：

  10.1021/jo052194c
• 作为产物：
  描述：

  4'-C-[(adenin-9-yl)methyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-thymidine 在 吡啶 、 咪唑 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 4'-C-[(N⁶-benzoyladenin-9-yl)-methyl]-thymidine
  参考文献：
  名称：

  Base−Base Interactions in the Minor Groove of Double-Stranded DNA

  摘要：

  A method has been developed for the synthesis of bisheaded nucleosides with thymine and adenine base moieties. We have demonstrated that, when incorporated in oligonucleotides, extrahelical A-T base interactions are possible when the bisheaded nucleosides are positioned in opposite strands of the duplex and are separated from each other by one regular base pair.

  DOI：

  10.1021/jo052194c

文献信息

• Base−Base Interactions in the Minor Groove of Double-Stranded DNA
  作者：Tongfei Wu、Koen Nauwelaerts、Arthur Van Aerschot、Matheus Froeyen、Eveline Lescrinier、Piet Herdewijn

  DOI：10.1021/jo052194c

  日期：2006.7.1

  A method has been developed for the synthesis of bisheaded nucleosides with thymine and adenine base moieties. We have demonstrated that, when incorporated in oligonucleotides, extrahelical A-T base interactions are possible when the bisheaded nucleosides are positioned in opposite strands of the duplex and are separated from each other by one regular base pair.