4-N-(8-nitronaphthalen-2-ylmethyl)-2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)cytidine | 857685-18-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 4-N-(8-nitronaphthalen-2-ylmethyl)-2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)cytidine
• 英文别名: 1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-4-[(8-nitronaphthalen-2-yl)methylamino]pyrimidin-2-one
• CAS: 857685-18-8
• 化学式: C₃₂H₄₈N₄O₆Si₂
• 分子量: 640.927
• InChiKey: FDDWIONVMIANFO-YIKNKFAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.62
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-N-(8-nitronaphthalen-2-ylmethyl)-2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)cytidine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 14.0h， 以48%的产率得到4-N-(8-aminonaphthalen-2-ylmethyl)-2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)cytidine
  参考文献：
  名称：

  Structure−Function Studies on a Synthetic Guanosine Receptor That Simultaneously Binds Watson−Crick and Hoogsteen Sites

  摘要：

  A series of receptors (11-16) designed to simultaneously bind the Watson-Crick and Hoogsteen sites of guanosine were synthesized, and their binding of guanosine tri-O-pentanoate (32) was probed via H-1 NMR complexation studies in 5% DMSO-d(6)-chloroform-d. The guanosine receptors were synthesized with aminonaphthalene or aminoquinoline auxiliary groups tethered to N-4 of cytosine via a methylene or carbonyl group. A structure -function relationship was established allowing energetic contributions made by components of nucleoside analogues to be probed and more general design rules formulated that may guide the development of more efficacious DNA bases.

  DOI：

  10.1021/jo0501689
• 作为产物：
  描述：

  2',3'-二-O-(叔-丁基二甲基硅烷基)-2'-脱氧胞苷 在 N,O-双三甲硅基乙酰胺 、 三乙胺-硼烷 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 25.25h， 生成 4-N-(8-nitronaphthalen-2-ylmethyl)-2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)cytidine
  参考文献：
  名称：

  Structure−Function Studies on a Synthetic Guanosine Receptor That Simultaneously Binds Watson−Crick and Hoogsteen Sites

  摘要：

  A series of receptors (11-16) designed to simultaneously bind the Watson-Crick and Hoogsteen sites of guanosine were synthesized, and their binding of guanosine tri-O-pentanoate (32) was probed via H-1 NMR complexation studies in 5% DMSO-d(6)-chloroform-d. The guanosine receptors were synthesized with aminonaphthalene or aminoquinoline auxiliary groups tethered to N-4 of cytosine via a methylene or carbonyl group. A structure -function relationship was established allowing energetic contributions made by components of nucleoside analogues to be probed and more general design rules formulated that may guide the development of more efficacious DNA bases.

  DOI：

  10.1021/jo0501689