2,3,4-tri-O-acetyl-N-(2,2-diethoxycarbonylvinyl)-6-O-<2',3',6'-tri-O-acetyl-4'-O-(2'',3'',4'',6''-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl>-β-D-glucopyranosylamine | 175022-49-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-acetyl-N-(2,2-diethoxycarbonylvinyl)-6-O-<2',3',6'-tri-O-acetyl-4'-O-(2'',3'',4'',6''-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl>-β-D-glucopyranosylamine
• CAS: 175022-49-8
• 化学式: C₄₆H₆₃NO₂₉
• 分子量: 1094.0
• InChiKey: UWKPFUNIJZQTSK-OOIOBHLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.26
• 重原子数：
  76.0
• 可旋转键数：
  23.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  373.78
• 氢给体数：
  1.0
• 氢受体数：
  30.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-N-(2,2-diethoxycarbonylvinyl)-6-O-<2',3',6'-tri-O-acetyl-4'-O-(2'',3'',4'',6''-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl>-β-D-glucopyranosylamine 在 氯 、 calcium carbonate 作用下， 以 氯仿 为溶剂， 反应 12.25h， 生成 2,3,4-tri-O-acetyl-6-O-<2',3',6'-tri-O-acetyl-4'-O-(2'',3'',4'',6''-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl>-β-D-glucopyranosyl isothiocyanate
  参考文献：
  名称：

  Stereoselective synthesis of nucleoside analogues of chiral imidazolidines from sugar isothiocyanates

  摘要：

  The syntheses of the disaccharide 5 and the trisaccharide 6 glycosyl isothiocyanates starting from di- or monosaccharide N-dialkoxycarbonylvinylglycosylamines 1 and 2 are described. Compounds 5, 6, alpha-(D-ribopyranosyl) and beta-(D-glucopyranosyl, D-ribopyranosyl) isothiocyanates and 1,3,4,6-tetra-O-acetyl-2-deoxy-2-isothiocyanato-beta-D-glucopyranose are; used in the diastereoselective synthesis of the nucleoside analogues of (5R)- and (5S)-5-hydroxyimidazolidine-2-thiones 7, 11, 14, 16, 17, 18a, and 18b. The 5R:5S ratio-depends on the anomeric configuration (configuration of C-2' for 18a, 18b) of the sugar isothiocyanate, beta-Glycosyl isothiocyanates give mostly the (5R)-epimer, whereas when a alpha-glycosyl isothiocyanate is used, there is practically no stereoselectivity.

  DOI：

  10.1016/0957-4166(95)00437-8
• 作为产物：
  描述：

  α-hepta-O-acetylmaltosyl bromide 、 2,3,4-tri-O-acetyl-6-O-trityl-N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine 在 calcium sulfate 、 silver perchlorate 作用下， 以 硝基甲烷 为溶剂， 反应 4.0h， 以27%的产率得到2,3,4-tri-O-acetyl-N-(2,2-diethoxycarbonylvinyl)-6-O-<2',3',6'-tri-O-acetyl-4'-O-(2'',3'',4'',6''-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl>-β-D-glucopyranosylamine
  参考文献：
  名称：

  Stereoselective synthesis of nucleoside analogues of chiral imidazolidines from sugar isothiocyanates

  摘要：

  The syntheses of the disaccharide 5 and the trisaccharide 6 glycosyl isothiocyanates starting from di- or monosaccharide N-dialkoxycarbonylvinylglycosylamines 1 and 2 are described. Compounds 5, 6, alpha-(D-ribopyranosyl) and beta-(D-glucopyranosyl, D-ribopyranosyl) isothiocyanates and 1,3,4,6-tetra-O-acetyl-2-deoxy-2-isothiocyanato-beta-D-glucopyranose are; used in the diastereoselective synthesis of the nucleoside analogues of (5R)- and (5S)-5-hydroxyimidazolidine-2-thiones 7, 11, 14, 16, 17, 18a, and 18b. The 5R:5S ratio-depends on the anomeric configuration (configuration of C-2' for 18a, 18b) of the sugar isothiocyanate, beta-Glycosyl isothiocyanates give mostly the (5R)-epimer, whereas when a alpha-glycosyl isothiocyanate is used, there is practically no stereoselectivity.

  DOI：

  10.1016/0957-4166(95)00437-8