1,2,5-Tri-O-acetyl-3,6-anhydro-α-D-mannofuranose | 71110-18-4

• 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: 1,2,5-Tri-O-acetyl-3,6-anhydro-α-D-mannofuranose
• 英文别名: 1,2,5-Tri-O-acetyl-3,6-anhydro-β-D-mannofuranose；Acetic acid (2R,3R,3aS,6S,6aR)-2,6-diacetoxy-hexahydro-furo[3,2-b]furan-3-yl ester；1,2,5-Tri-O-acetyl-3,6-anhydro-β-D-glucofuranose；Acetic acid (2S,3R,3aS,6S,6aR)-2,6-diacetoxy-hexahydro-furo[3,2-b]furan-3-yl ester；1,2,5-Tri-O-acetyl-3,6-anhydro-β-L-gulofuranose；1,2,5-Tri-O-acetyl-3,6-anhydro-α-L-gulofuranose；1,2,5-Tri-O-acetyl-3,6-anhydro-α-D-glucofuranose；1,2,5-tri-O-acetyl-3,6-anhydro-D-glucofuranose
• CAS: 71110-18-4；71110-19-5；87596-12-1；87596-13-2；87596-14-3；87596-15-4；87596-16-5；87596-17-6
• 化学式: C₁₂H₁₆O₈
• 分子量: 288.254
• InChiKey: OSLJEKZLNKFHTN-ZLZKJVMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.46
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,2,5-Tri-O-acetyl-3,6-anhydro-α-D-mannofuranose 在 氢溴酸 、 氰化汞 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 2-((14-hydroxy-10,13-dimethyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)hexahydrofuro[3,2-b]furan-3,6-diyl diacetate
  参考文献：
  名称：

  Digitoxigenin 3-O-.beta.-D-furanosides

  摘要：

  The syntheses of the title compounds were accomplished by Koenig-Knorr condensation of acylated furanoses with digitoxigenin followed by basic hydrolysis of protecting groups. In this manner the riboside, 5-amino-5-deoxyriboside, 3,6-anhydroglucoside, and 3,6-dideoxy-3,6-iminoglucoside of digitoxigenin were prepared. These compounds as well as several of the synthetic intermediates showed weak to moderate cardiotonic activity.

  DOI：

  10.1021/jm00152a012
• 作为产物：
  描述：

  5-O-acetyl-3,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose 在 吡啶 、 Dowex AG-50 X₈ 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 1,2,5-Tri-O-acetyl-3,6-anhydro-α-D-mannofuranose
  参考文献：
  名称：

  Digitoxigenin 3-O-.beta.-D-furanosides

  摘要：

  The syntheses of the title compounds were accomplished by Koenig-Knorr condensation of acylated furanoses with digitoxigenin followed by basic hydrolysis of protecting groups. In this manner the riboside, 5-amino-5-deoxyriboside, 3,6-anhydroglucoside, and 3,6-dideoxy-3,6-iminoglucoside of digitoxigenin were prepared. These compounds as well as several of the synthetic intermediates showed weak to moderate cardiotonic activity.

  DOI：

  10.1021/jm00152a012