dimethyl 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]triazole-4,5-dicarboxylate | 225094-88-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: dimethyl 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]triazole-4,5-dicarboxylate
• CAS: 225094-88-2
• 化学式: C₁₁H₁₅N₃O₆S
• 分子量: 317.323
• InChiKey: GBKBIAMIYHBWQE-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  dimethyl 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]triazole-4,5-dicarboxylate 在 氨 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以90%的产率得到2'-deoxy-4'-thio-1'-[4,5-bis(carbamoyl)-1,2,3-triazole]-β-D-erythro-pentofuranoside
  参考文献：
  名称：

  Novel Triazole 2′-Deoxy-4′-thionucleosides: Stereoselective Synthesis and Biological Evaluation

  摘要：

  A study on the use of protecting groups led to the employment of the para-methoxybenzoyl (pMB) group as a directing group in the synthesis of novel triazole 2'-deoxy-4'-thionucleosides. Use of the pMB group gave alpha:beta ratios of 1:6 in the glycosylation step with azidotrimethylsilane. A series of novel triazoles were generated for in vitro antiviral evaluation.

  DOI：

  10.1080/15257779908043089
• 作为产物：
  描述：

  [(2R,3S)-5-acetyloxy-3-(4-methoxybenzoyl)oxythiolan-2-yl]methyl 4-methoxybenzoate 在 三氟甲磺酸三甲基硅酯 、 叠氮基三甲基硅烷 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 22.5h， 生成 dimethyl 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]triazole-4,5-dicarboxylate
  参考文献：
  名称：

  Novel Triazole 2′-Deoxy-4′-thionucleosides: Stereoselective Synthesis and Biological Evaluation

  摘要：

  A study on the use of protecting groups led to the employment of the para-methoxybenzoyl (pMB) group as a directing group in the synthesis of novel triazole 2'-deoxy-4'-thionucleosides. Use of the pMB group gave alpha:beta ratios of 1:6 in the glycosylation step with azidotrimethylsilane. A series of novel triazoles were generated for in vitro antiviral evaluation.

  DOI：

  10.1080/15257779908043089