N-[1-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-hydroxy-4-triethylsilyloxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide | 1453190-11-8

• 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: N-[1-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-hydroxy-4-triethylsilyloxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 1453190-11-8
• 化学式: C₄₃H₄₉N₃O₈Si
• 分子量: 763.963
• InChiKey: IPRHQVXKLLSFGV-SSLBRWRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.17
• 重原子数：
  55
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  三乙基氯硅烷 、 5'-dimethoxytrityl N-benzoylcytidine 在 C₁₇H₂₉N₃O₂ 、 N,N-二异丙基乙胺盐酸盐 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以86%的产率得到N-[1-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-hydroxy-4-triethylsilyloxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
  参考文献：
  名称：

  Practical Silyl Protection of Ribonucleosides

  摘要：

  Herein we report the site-selective silylation of the ribonucelosides. The method enables a simple and efficient procedure for accessing suitably protected monomers for automated RNA synthesis. Switching to the opposite enantiomer of the catalyst allows for the selective silylation of the 3'-hydroxyl, which could be used in the synthesis of unnatural RNA or for the analoging of ribonucelosides. Lastly, the procedure was extended to ribavirin a potent antiviral therapeutic.

  DOI：

  10.1021/ol402023c

文献信息

• Practical Silyl Protection of Ribonucleosides
  作者：Thomas P. Blaisdell、Sunggi Lee、Pinar Kasaplar、Xixi Sun、Kian L. Tan

  DOI：10.1021/ol402023c

  日期：2013.9.20

  Herein we report the site-selective silylation of the ribonucelosides. The method enables a simple and efficient procedure for accessing suitably protected monomers for automated RNA synthesis. Switching to the opposite enantiomer of the catalyst allows for the selective silylation of the 3'-hydroxyl, which could be used in the synthesis of unnatural RNA or for the analoging of ribonucelosides. Lastly, the procedure was extended to ribavirin a potent antiviral therapeutic.