5-O-(3-O-acetyl-5-azido-5-deoxyl-2-O-methyl-β-D-ribofuranosyl)-1-deoxy-1-(3-(benzyloxymethyl)uracil-1-yl)-2,3-O-cyclopentanylidene-5-C-ethynyl-β-ribofuranose | 1067674-62-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-(3-O-acetyl-5-azido-5-deoxyl-2-O-methyl-β-D-ribofuranosyl)-1-deoxy-1-(3-(benzyloxymethyl)uracil-1-yl)-2,3-O-cyclopentanylidene-5-C-ethynyl-β-ribofuranose
• 英文别名: [(2R,3R,4R,5R)-5-[(1S)-1-[(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]prop-2-ynoxy]-2-(azidomethyl)-4-methoxyoxolan-3-yl] acetate
• CAS: 1067674-62-7
• 化学式: C₃₂H₃₇N₅O₁₁
• 分子量: 667.673
• InChiKey: DLJLBXDMBDURID-YHIIUUKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  146
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  p-tolyl 3-O-acetyl-5-azido-5-deoxyl-2-O-methyl-1-thio-β-D-ribofuranoside 、 3-((benzyloxy)methyl)-1-((3a'R,4'R,6'R,6a'R)-4'-((S)-1-hydroxyprop-2-yn-1-yl)tetrahydrospiro[cyclopentane-1,2'-furo[3,4-d][1,3]dioxol]-6'-yl)pyrimidine-2,4(1H,3H)-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， 生成 5-O-(3-O-acetyl-5-azido-5-deoxyl-2-O-methyl-β-D-ribofuranosyl)-1-deoxy-1-(3-(benzyloxymethyl)uracil-1-yl)-2,3-O-cyclopentanylidene-5-C-ethynyl-β-ribofuranose 、 5-O-(3-O-acetyl-5-azido-5-deoxyl-2-O-methyl-α-D-ribofuranosyl)-1-deoxy-1-(3-(benzyloxymethyl)uracil-1-yl)-2,3-O-cyclopentanylidene-5-C-ethynyl-β-ribofuranose
  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