5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-phthalimidoethyl)-N²-isobutyrylguanosine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoroamidite | 1037523-45-7

• 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: 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-phthalimidoethyl)-N²-isobutyrylguanosine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoroamidite
• 英文别名: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-3-[2-(1,3-dioxoisoindol-2-yl)ethoxy]oxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• CAS: 1037523-45-7
• 化学式: C₅₄H₆₁N₈O₁₁P
• 分子量: 1029.1
• InChiKey: PKGWGGHWBXBYHB-ZQRZYEQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  74
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  217
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-phthalimidoethyl)-N²-isobutyrylguanosine 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 4,5-二氰基咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以72%的产率得到5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-phthalimidoethyl)-N²-isobutyrylguanosine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoroamidite
  参考文献：
  名称：

  Preparation of Zwitterionic Ribonucleoside Phosphoramidites for Solid-Phase siRNA Synthesis

  摘要：

  RNA oligomers, carrying 2'-O-modified nucleosides, proved to be extremely useful in different antisense strategies, including RNAi. The 2'-O-alkyl modification, carrying an amino functionality, deserves special attention due to its ability to neutralize the negatively charged phosphate backbone, leading to improved physicochemical and pharmaceutical properties of antisense agents. Here, we report a very short, convenient, and straightforward synthesis of phosphoramidites for all four 2'-aminoethyl-modified natural ribonucleosides, where the aminoethyl group is introduced in a single alkylation step.

  DOI：

  10.1021/jo800451m