N⁶-<(Allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 3'-(ethyl N,N-diisopropylphosphoramidite)

• 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: N⁶-<(Allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 3'-(ethyl N,N-diisopropylphosphoramidite)
• 英文别名: prop-2-enyl N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[[di(propan-2-yl)amino]-ethoxyphosphanyl]oxyoxolan-2-yl]purin-6-yl]carbamate
• 化学式: C₄₃H₅₃N₆O₈P
• 分子量: 812.903
• InChiKey: WRMNTTWWDKLDDL-MACIYHSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  58
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  N⁶-<(Allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 、 ethyl (N,N,N',N'-tetraisopropyl)phosphorodiamidite 在 四氮唑 、 二乙胺 作用下， 以 乙腈 为溶剂， 以67%的产率得到N⁶-<(Allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 3'-(ethyl N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  General Synthesis and Binding Affinity of Position-Selective Phosphonodiester- and Phosphotriester-Incorporated Oligodeoxyribonucleotides

  摘要：

  Synthesis of phosphonodiester- and phosphotriester-modified oligodeoxyribonucleotides has been accomplished via the phosphoramidite approach with allylic protection. The modification can be made at the selected position(s) of the oligomers. The efficiency of this method has been demonstrated by the synthesis of base-labile modified oligo(deoxyribonucleotide)s such as the methyl phosphates and phenylphosphonates. Melting temperatures of the duplexes containing these artificial strands indicate that the backbone-alternation, which is made at a single site, does not have a negative influence on the binding affinity to the complementary DNA.

  DOI：

  10.1021/jo00109a024