2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine | 199792-80-8

• 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: 2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine
• 英文别名: 2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine
• CAS: 199792-80-8
• 化学式: C₂₇H₃₈N₆O₇Si
• 分子量: 586.72
• InChiKey: YLPWDYMDVJPUSV-BHDDXSALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  163.76
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine 在 吡啶 、 四氮唑 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 291.0h， 生成 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine 5'-(2-cyanoethyl diisopropylphosphoramidite)
  参考文献：
  名称：

  核苷酸，第 LXV 部分，2'-脱氧核糖核苷 5'-亚磷酰胺的合成：反向 (5'-3')-寡核苷酸方法的新构件

  摘要：

  The syntheses of the 3'-O-(4,4'-dimethoxytrityl)-protected 5'-phosphoramidites 25-28 and 5'-(hydrogen succinates) 29-32, which can be used as monomeric building blocks for the inverse (5'-3')-oligodeoxyribonucleotide synthesis are described (Scheme). These activated nucleosides and nucleotides were obtained by two slightly different four-step syntheses starting with the base-protected nucleosides 13-20. For the protection of the aglycon residues, the well-established 2-(4-nitrophenyl)ethyl (npe) and [2-(4-nitrophenyl)ethoxy]carbonyl (npeoc) groups were used. The assembly of the oligonucleotides required a slightly increased coupling time of 3 min in application of the common protocol (see Table 1). The use of pyridinium hydrochloride as an activator (instead of 1H-tetrazole) resulted in an extremely shorter activation time of 30 seconds. We established the efficiency of this inverse strategy by the synthesis of the oligonucleotide 3'-conjugates 33 and 34 which carry lipophilic caps derived from cholesterol and vitamin E, respectively, as well as by the formation of (3'-3')- and (5'-5')-internucleotide linkages (see Table 2).

  DOI：

  10.1002/1522-2675(20000809)83:8<2023::aid-hlca2023>3.0.co;2-p
• 作为产物：
  描述：

  二甲基叔己基氯化硅 、 2'-deoxy-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以17%的产率得到2'-deoxy-3',5'-bis-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine
  参考文献：
  名称：

  An Inverse Approach in Oligodeoxyribonucleotide Synthesis

  摘要：

  We synthesized 3'-O-dimethoxytrityl-5'O-phosphoramidites and 5'-O-succinates which can be used as monomeric building blocks for the built up of oligodeoxyribonucleotides in the alternative 5'-3' direction. With this inverse strategy oligonucleotide 3'-conjugates as well as 3'-3' and 5'-5' internucleotidic linkages can be easily formed.

  DOI：

  10.1080/07328319708006249