1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]uracil | 289891-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]uracil
• CAS: 289891-33-4
• 化学式: C₃₆H₄₁BrN₂O₉
• 分子量: 725.634
• InChiKey: PBUUCOHPDYYNNP-ZBVHFZKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  48.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  141.47
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]uracil 在 二丁基二氯化锡 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 1.75h， 生成 1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]uracil 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：

  [(2S,3R,4R)-4,5-dibenzoyloxy-2-[(1R)-2-(5-bromopentoxy)-1-tri(propan-2-yl)silyloxyethyl]oxolan-3-yl] benzoate 在 2,4,6-三甲基吡啶 、 盐酸 、 sodium hydroxide 、 氢氟酸 、 四氯化锡 、 silver nitrate 、 牛血清白蛋白 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 10.33h， 生成 1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]uracil
  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