6-methoxy-2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosylmercapto)-1,3-benzothiazole | 676617-94-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-methoxy-2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosylmercapto)-1,3-benzothiazole
• 英文别名: [(2R,3R,4R,5S)-3,4-diacetyloxy-5-[(6-methoxy-1,3-benzothiazol-2-yl)sulfanyl]oxolan-2-yl]methyl acetate
• CAS: 676617-94-0
• 化学式: C₁₉H₂₁NO₈S₂
• 分子量: 455.51
• InChiKey: RFBJLKHYMFNIIT-DDBAPUKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  164
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-methoxy-2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosylmercapto)-1,3-benzothiazole 在 氨 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以88%的产率得到6-methoxy-2-(β-D-ribofuranosyl)-1,3-benzothiazole
  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：

  2-巯基-6-甲氧基苯并噻唑 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 6-methoxy-2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosylmercapto)-1,3-benzothiazole
  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