p-tolyl 3-O-acetyl-2-O-methyl-1-thio-5-O-triisopropylsilyl-β-D-ribofuranoside | 1067674-74-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 3-O-acetyl-2-O-methyl-1-thio-5-O-triisopropylsilyl-β-D-ribofuranoside
• 英文别名: [(2R,3R,4R,5S)-4-methoxy-5-(4-methylphenyl)sulfanyl-2-[tri(propan-2-yl)silyloxymethyl]oxolan-3-yl] acetate
• CAS: 1067674-74-1
• 化学式: C₂₄H₄₀O₅SSi
• 分子量: 468.73
• InChiKey: JCVOEKSBMZSIRN-YCAMKHIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-tolyl 3-O-acetyl-2-O-methyl-1-thio-5-O-triisopropylsilyl-β-D-ribofuranoside 在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 p-tolyl 3-O-acetyl-2-O-methyl-1-thio-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：

  、 乙酸酐 在 吡啶 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以0.138 mmol的产率得到p-tolyl 3-O-acetyl-2-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