4'-C-[(adenin-9-yl)methyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-thymidine | 879015-09-5

• 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-[(adenin-9-yl)methyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-thymidine
• 英文别名: 1-[(2R,4S,5R)-5-[(6-aminopurin-9-yl)methyl]-4-[tert-butyl(dimethyl)silyl]oxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 879015-09-5
• 化学式: C₂₂H₃₃N₇O₅Si
• 分子量: 503.633
• InChiKey: IXKVPKMCAZBATD-SMASLZHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  158
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3'-O-(tert-butyldimethylsilyl)-4'-(hydroxymethyl)-thymidine 在 吡啶 、 sodium hydroxide 、 18-冠醚-6 、 sodium hydride 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 4'-C-[(adenin-9-yl)methyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-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.