[(2R,3R,4R,5R)-5-[[(3aR,4R,6R,6aR)-4-[2,4-dioxo-3-(phenylmethoxymethyl)pyrimidin-1-yl]spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclopentane]-6-yl]methoxy]-2-(azidomethyl)-4-benzoyloxyoxolan-3-yl] benzoate | 1067674-53-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4R,5R)-5-[[(3aR,4R,6R,6aR)-4-[2,4-dioxo-3-(phenylmethoxymethyl)pyrimidin-1-yl]spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclopentane]-6-yl]methoxy]-2-(azidomethyl)-4-benzoyloxyoxolan-3-yl] benzoate
• CAS: 1067674-53-6
• 化学式: C₄₁H₄₁N₅O₁₂
• 分子量: 795.803
• InChiKey: YAHSWEQMYFDFBK-IUXNROIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  58
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  163
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  p-methylphenyl 5-deoxy-5-azido-2,3-di-O-benzoyl-1-thio-β-D-ribofuranose 、 1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclopentane]-4-yl]-3-(phenylmethoxymethyl)pyrimidine-2,4-dione 在 strontium(II) carbonate 、 silver trifluoromethanesulfonate 、 p-toluolsulfenyl bromide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以85%的产率得到[(2R,3R,4R,5R)-5-[[(3aR,4R,6R,6aR)-4-[2,4-dioxo-3-(phenylmethoxymethyl)pyrimidin-1-yl]spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclopentane]-6-yl]methoxy]-2-(azidomethyl)-4-benzoyloxyoxolan-3-yl] benzoate
  参考文献：
  名称：

  Highly Efficient O-Glycosylations with p-Tolyl Thioribosides and p-TolSOTf

  摘要：

  GraphicsA wide variety of p-tolyl thioriboside donors are examined for O-ribosylations of primary and secondary alcohols. p-Tolylsulfenyl trifluoromethanesulfonate (p-TolSOTf) is very effective in promoting O-ribosylations with p-tolyl thioriboside; all reactions are completed within 1-15 min to provide the desired products in good yield with reliable alpha/beta selectivity. A wide range of functional groups are tolerated under these conditions. The described O-ribosylation conditions are very useful for the generation of ribosaminouridine library molecules in solution or on polymer support.

  DOI：

  10.1021/jo801408x

文献信息

• Highly Efficient <i>O</i>-Glycosylations with <i>p</i>-Tolyl Thioribosides and <i>p</i>-TolSOTf
  作者：Michio Kurosu、Kai Li

  DOI：10.1021/jo801408x

  日期：2008.12.19

  GraphicsA wide variety of p-tolyl thioriboside donors are examined for O-ribosylations of primary and secondary alcohols. p-Tolylsulfenyl trifluoromethanesulfonate (p-TolSOTf) is very effective in promoting O-ribosylations with p-tolyl thioriboside; all reactions are completed within 1-15 min to provide the desired products in good yield with reliable alpha/beta selectivity. A wide range of functional groups are tolerated under these conditions. The described O-ribosylation conditions are very useful for the generation of ribosaminouridine library molecules in solution or on polymer support.