2,3,4-tri-O-acetyl-6-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranosylamine | 175022-50-1

• 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-6-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranosylamine
• CAS: 175022-50-1
• 化学式: C₂₆H₃₇NO₁₇
• 分子量: 635.576
• InChiKey: VUXMAYFDFYRPKC-PCIRLDFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.44
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  237.81
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-6-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranosylamine 在 calcium carbonate 作用下， 以 氯仿 、 水 、 丙酮 为溶剂， 反应 5.0h， 生成 (4R,5R)-5-hydroxy-1-<2',3',4'-tri-O-acetyl-6-O-(2''',3''',4''',6'''-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranosyl>-4-(D-arabinotetritol-1-yl)imidazolidine-2-thione
  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：

  2,3,4-tri-O-acetyl-N-(2,2-diethoxycarbonylvinyl)-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranosylamine 在 氯 作用下， 以 氯仿 为溶剂， 反应 0.25h， 生成 2,3,4-tri-O-acetyl-6-O-(2',3',4',6'-tetra-O-acetyl-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