N6-benzoyl-9-[2',3'-di-O-benzoyl-6'-O-(5-bromopentyl)-β-D-allofuranosyl]adenine | 289891-32-3

• 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: N6-benzoyl-9-[2',3'-di-O-benzoyl-6'-O-(5-bromopentyl)-β-D-allofuranosyl]adenine
• 英文别名: N⁶-benzoyl-9-[2',3'-di-O-benzoyl-6'-O-(5-bromopentyl)-β-D-allofuranosyl]adenine
• CAS: 289891-32-3
• 化学式: C₃₇H₃₆BrN₅O₈
• 分子量: 758.626
• InChiKey: YKPZTATUHDTIMI-JVMUSOSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  51.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  163.99
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N6-benzoyl-9-[2',3'-di-O-benzoyl-6'-O-(5-bromopentyl)-β-D-allofuranosyl]adenine 在 2,4,6-三甲基吡啶 、 sodium hydroxide 、 二丁基二氯化锡 、 silver nitrate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 3.25h， 生成 N⁶-benzoyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]adenine 3'-(2-cyanoethyl diisopropylphosphoramidite)
  参考文献：
  名称：

  摘要：

  The preparation of building blocks for the incorporation of 6'-0-(5-bromopentyl)-substituted beta-D-allofuranosylnucleosides and 2'-O-[(3-bromopropoxy)methyl]-substituted ribonucleosides into oligonucleotide sequences is presented (Schemes 1 and 2). These reactive building blocks can be modified with a variety of soft nucleophiles while the (fully protected) sequence is still attached to the solid support. As an example of this strategy, we carried out some preliminary solid-phase substitution and conjugation reactions with DNA sequences containing a 2'-O-[(3-bromopropoxy)methyl]-substituted ribonucleoside (Scheme 3) and determined the pairing properties of duplexes obtained therefrom.

  DOI：

  10.1002/1522-2675(20000607)83:6<1127::aid-hlca1127>3.0.co;2-b
• 作为产物：
  描述：

  N6-苯甲酰基腺嘌呤 在 四氯化锡 、 牛血清白蛋白 、 三氟乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 13.33h， 生成 N6-benzoyl-9-[2',3'-di-O-benzoyl-6'-O-(5-bromopentyl)-β-D-allofuranosyl]adenine
  参考文献：
  名称：

  摘要：

  The preparation of building blocks for the incorporation of 6'-0-(5-bromopentyl)-substituted beta-D-allofuranosylnucleosides and 2'-O-[(3-bromopropoxy)methyl]-substituted ribonucleosides into oligonucleotide sequences is presented (Schemes 1 and 2). These reactive building blocks can be modified with a variety of soft nucleophiles while the (fully protected) sequence is still attached to the solid support. As an example of this strategy, we carried out some preliminary solid-phase substitution and conjugation reactions with DNA sequences containing a 2'-O-[(3-bromopropoxy)methyl]-substituted ribonucleoside (Scheme 3) and determined the pairing properties of duplexes obtained therefrom.

  DOI：

  10.1002/1522-2675(20000607)83:6<1127::aid-hlca1127>3.0.co;2-b