2'-O-(2-phthalimidoethyl)uridine | 1037523-24-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2'-O-(2-phthalimidoethyl)uridine
• 英文别名: 2-[2-[(2R,3R,4R,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxyethyl]isoindole-1,3-dione
• CAS: 1037523-24-2
• 化学式: C₁₉H₁₉N₃O₈
• 分子量: 417.375
• InChiKey: HCIHTVNLXLWJPG-SCFUHWHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'-O-(2-phthalimidoethyl)uridine 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 作用下， 反应 3.0h， 以86%的产率得到5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-phthalimidoethyl)uridine
  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
• 作为产物：
  描述：

  3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-(2-phthalimidoethyl)uridine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以78%的产率得到2'-O-(2-phthalimidoethyl)uridine
  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

文献信息

• Preparation of Zwitterionic Ribonucleoside Phosphoramidites for Solid-Phase siRNA Synthesis
  作者：Romualdas Smicius、Joachim W. Engels

  DOI：10.1021/jo800451m

  日期：2008.7.1

  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.