Acetic acid (2R,3R,4R)-4-acetoxy-5-bromo-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester | 66074-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Acetic acid (2R,3R,4R)-4-acetoxy-5-bromo-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester
• CAS: 66074-47-3
• 化学式: C₁₆H₁₉BrO₈S
• 分子量: 451.292
• InChiKey: VNULBLBDVOBJBD-SLCRAUQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R)-4-acetoxy-5-bromo-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester 在 叠氮化锂 、 氰化汞 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.0h， 生成 3-O-(2,3-di-O-acetyl-5-azido-5-deoxy-β-D-ribofuranosyl)digitoxigenin
  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：

  1,2,3-tri-O-acetyl-5-O-(p-tolylsulfonyl)-D-ribofuranose 在 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 Acetic acid (2R,3R,4R)-4-acetoxy-5-bromo-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester
  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