p-tolyl 2,3-di-O-methyl-1-thio-5-O-triisopropylsilyl-β-D-ribofuranoside | 1067674-71-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 2,3-di-O-methyl-1-thio-5-O-triisopropylsilyl-β-D-ribofuranoside
• 英文别名: [(2R,3R,4R,5S)-3,4-dimethoxy-5-(4-methylphenyl)sulfanyloxolan-2-yl]methoxy-tri(propan-2-yl)silane
• CAS: 1067674-71-8
• 化学式: C₂₃H₄₀O₄SSi
• 分子量: 440.72
• InChiKey: LKVQXFDIRCOTHS-ODAXIHTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  p-tolyl 2,3-di-O-methyl-1-thio-5-O-triisopropylsilyl-β-D-ribofuranoside 、 2-丙炔-1-醇 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， 生成 propargyl 2,3-di-O-methyl-5-O-triisopropanylsilyl-α-D-ribofuranoside 、 propargyl 2,3-di-O-methyl-5-O-triisopropanylsilyl-β-D-ribofuranoside
  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
• 作为产物：
  描述：

  (2S,3R,4S,5R)-2-(p-tolylthio)-5-(((triisopropylsilyl)oxy)methyl)tetrahydrofuran-3,4-diol 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 p-tolyl 2,3-di-O-methyl-1-thio-5-O-triisopropylsilyl-β-D-ribofuranoside
  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.