(3R,4S,5R)-4-(allyloxy)-5-((((2R,3S,4R)-4,5-diacetoxy-2-(methoxymethyl)tetrahydrofuran-3-yl)oxy)methyl)tetrahydrofuran-2,3-diyl diacetate | 1050411-96-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5R)-4-(allyloxy)-5-((((2R,3S,4R)-4,5-diacetoxy-2-(methoxymethyl)tetrahydrofuran-3-yl)oxy)methyl)tetrahydrofuran-2,3-diyl diacetate
• CAS: 1050411-96-5
• 化学式: C₂₂H₃₂O₁₃
• 分子量: 504.488
• InChiKey: WSULICCVUDGZRB-XQMGZCRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.03
• 重原子数：
  35.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  151.35
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-4-(allyloxy)-5-((((2R,3S,4R)-4,5-diacetoxy-2-(methoxymethyl)tetrahydrofuran-3-yl)oxy)methyl)tetrahydrofuran-2,3-diyl diacetate 、 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79%的产率得到[(2R,3R,4S,5R)-4-[[(2R,3S,4R,5R)-4-acetyloxy-5-(2,4-dioxopyrimidin-1-yl)-3-prop-2-enoxyoxolan-2-yl]methoxy]-2-(2,4-dioxopyrimidin-1-yl)-5-(methoxymethyl)oxolan-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
• 作为产物：
  描述：

  、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 4.0h， 生成 (3R,4S,5R)-4-(allyloxy)-5-((((2R,3S,4R)-4,5-diacetoxy-2-(methoxymethyl)tetrahydrofuran-3-yl)oxy)methyl)tetrahydrofuran-2,3-diyl diacetate
  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