N⁴-acetyl-2'-O-[(3-bromopropoxy)methyl]-5'-O-(4,4'-dimethoxytrityl)cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite) | 289891-54-9

• 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: N⁴-acetyl-2'-O-[(3-bromopropoxy)methyl]-5'-O-(4,4'-dimethoxytrityl)cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite)
• 英文别名: N-[1-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-(3-bromopropoxymethoxy)-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
• CAS: 289891-54-9
• 化学式: C₄₅H₅₇BrN₅O₁₀P
• 分子量: 938.853
• InChiKey: KCCYTMDTKDTKMC-TYYNOMDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  62
• 可旋转键数：
  24
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  163
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  5’-O-(4,4’-二甲氧基三苯甲基)-N4-乙酰基-2’-脱氧胞苷 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， 生成 N⁴-acetyl-2'-O-[(3-bromopropoxy)methyl]-5'-O-(4,4'-dimethoxytrityl)cytidine 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

文献信息

• ——
  作者：Xiaolin Wu、Stefan Pitsch

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

  日期：2000.6.7

  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.