(2S,3R,4S,5R)-2-(p-tolylthio)-5-(((triisopropylsilyl)oxy)methyl)tetrahydrofuran-3,4-diol | 1131611-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R)-2-(p-tolylthio)-5-(((triisopropylsilyl)oxy)methyl)tetrahydrofuran-3,4-diol
• CAS: 1131611-85-2
• 化学式: C₂₁H₃₆O₄SSi
• 分子量: 412.666
• InChiKey: KHDOXIUKDBXHLT-NCYKPQTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R)-2-(p-tolylthio)-5-(((triisopropylsilyl)oxy)methyl)tetrahydrofuran-3,4-diol 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以1.02 g的产率得到p-tolyl 2,3-di-O-benzyl-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
• 作为产物：
  描述：

  三异丙基氯硅烷 、 p-tolyl 1-thio-β-D-ribofuranoside 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (2S,3R,4S,5R)-2-(p-tolylthio)-5-(((triisopropylsilyl)oxy)methyl)tetrahydrofuran-3,4-diol
  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