(3aR,5R,6S,6aR)-5-[[(3aR,5R,6S,6aR)-5-(methoxymethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxymethyl]-2,2-dimethyl-6-prop-2-enoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole | 1050411-93-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5R,6S,6aR)-5-[[(3aR,5R,6S,6aR)-5-(methoxymethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxymethyl]-2,2-dimethyl-6-prop-2-enoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 1050411-93-2
• 化学式: C₂₀H₃₂O₉
• 分子量: 416.469
• InChiKey: UCTOZYNMIGWTRG-VMAIWCPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6S,6aR)-5-[[(3aR,5R,6S,6aR)-5-(methoxymethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxymethyl]-2,2-dimethyl-6-prop-2-enoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole 在 硫酸 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成
  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：

  [(3aR,5R,6S,6aR)-6-((3aR,5R,6S,6aR)-6-Allyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-methanol 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以91%的产率得到(3aR,5R,6S,6aR)-5-[[(3aR,5R,6S,6aR)-5-(methoxymethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxymethyl]-2,2-dimethyl-6-prop-2-enoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
  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