(2R,3R,4R,5R)-4-(((2R,3R,4R,5R)-4-acetoxy-3-(allyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methoxy)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-(methoxymethyl)tetrahydrofuran-3-yl acetate | 1050412-23-1

• 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: (2R,3R,4R,5R)-4-(((2R,3R,4R,5R)-4-acetoxy-3-(allyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methoxy)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-(methoxymethyl)tetrahydrofuran-3-yl acetate
• CAS: 1050412-23-1
• 化学式: C₂₆H₃₂N₄O₁₃
• 分子量: 608.559
• InChiKey: OFNDPEOBTVEMSW-KDMXBIESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.65
• 重原子数：
  43.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  208.47
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  、 尿嘧啶 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以0.3 g的产率得到(2R,3R,4R,5R)-4-(((2R,3R,4R,5R)-4-acetoxy-3-(allyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methoxy)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-(methoxymethyl)tetrahydrofuran-3-yl acetate
  参考文献：
  名称：

  Synthesis of Ether-Linked Oligoribo- and Xylonucleosides from 3,5′-Ether-Linked Pseudosaccharides

  摘要：

  First examples of di- and trinucleosides with ribose and xylose stereochemistry having internucleoside ether linkage were synthesized from 3,5'-ether-linked pseudosaccharides. The synthetic protocol involved removal of 1,2-isopropylidene protecting groups front the pseudosaccharides followed by acetylation and a subsequent Vorbruggen transglycosylation with uracil and N-benzoylaminopurine. The synthetic strategy is potentially important for the development of RNA analogues with internucleoside ether linkage.

  DOI：

  10.1021/jo8007429