4'-C-[(adenin-9-yl)methyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-O²,5'-anhydrothymidine | 879015-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 4'-C-[(adenin-9-yl)methyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-O²,5'-anhydrothymidine
• 英文别名: (1R,10R,11S)-10-[(6-aminopurin-9-yl)methyl]-11-[tert-butyl(dimethyl)silyl]oxy-4-methyl-8,13-dioxa-2,6-diazatricyclo[8.2.1.02,7]trideca-3,6-dien-5-one
• CAS: 879015-08-4
• 化学式: C₂₂H₃₁N₇O₄Si
• 分子量: 485.618
• InChiKey: GELURTPHPAZLAP-SMASLZHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4'-C-[(adenin-9-yl)methyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-O²,5'-anhydrothymidine 在 吡啶 、 咪唑 、 sodium hydroxide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 4.5h， 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 、 18-冠醚-6 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 4'-C-[(adenin-9-yl)methyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-O²,5'-anhydrothymidine
  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.