2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosylmercapto)pyridine | 69493-87-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosylmercapto)pyridine
• CAS: 69493-87-4
• 化学式: C₁₆H₁₉NO₇S
• 分子量: 369.395
• InChiKey: UMTQVZYRDJSQRF-MIGQKNRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  25.0
• 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：
  101.02
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosylmercapto)pyridine 在 氨 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以90%的产率得到2-(β-D-ribofuranosylmercapto)pyridine
  参考文献：
  名称：

  A New Approach to the Synthesis of Benzothiazole, Benzoxazole, and Pyridine Nucleosides as Potential Antitumor Agents

  摘要：

  A modified nitrogen and sulfur glycosylation reaction involving benzothiazole benzoxazole and pyridine nucleoside bases with furanose and pyranose sugars are described. Conformational analysis has been studied by homo- and hetero-nuclear two-dimensional NMR methods (2D DFQ-COSY, HMQC and HMBC). The N and S sites of glycosylation were determined from the H-1, C-13 hetero-nuclear multiple-quantum coherence (HMQC) experiments. All the deprotected nucleosides were tested for their potential antitumor activity.

  DOI：

  10.1081/ncn-120026407
• 作为产物：
  描述：

  <(trimethylsilyl)thio>pyridine 、 四乙酰核糖 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以1.77 g的产率得到2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosylmercapto)pyridine
  参考文献：
  名称：

  A New Approach to the Synthesis of Benzothiazole, Benzoxazole, and Pyridine Nucleosides as Potential Antitumor Agents

  摘要：

  A modified nitrogen and sulfur glycosylation reaction involving benzothiazole benzoxazole and pyridine nucleoside bases with furanose and pyranose sugars are described. Conformational analysis has been studied by homo- and hetero-nuclear two-dimensional NMR methods (2D DFQ-COSY, HMQC and HMBC). The N and S sites of glycosylation were determined from the H-1, C-13 hetero-nuclear multiple-quantum coherence (HMQC) experiments. All the deprotected nucleosides were tested for their potential antitumor activity.

  DOI：

  10.1081/ncn-120026407