3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyloxy)-2-(tert-butoxycarbonylamino)-propionic acid benzyl ester | 1067674-89-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyloxy)-2-(tert-butoxycarbonylamino)-propionic acid benzyl ester
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxo-3-phenylmethoxypropoxy]oxolan-2-yl]methyl benzoate
• CAS: 1067674-89-8
• 化学式: C₄₁H₄₁NO₁₂
• 分子量: 739.776
• InChiKey: ZLTAKBKUWPSBPV-RQZYVOLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  54
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  p-tolyl 2,3,5-tri-O-benzoyl-1-thio-D-ribofuranoside 、 N-叔丁氧羰基-L-丝氨酸 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95%的产率得到3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyloxy)-2-(tert-butoxycarbonylamino)-propionic acid benzyl ester
  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.