1,5-di-O-acetyl-3-(1,2,4-triazol-1-yl)-2,3,6-trideoxy-L-arabino-hexofuranose | 142137-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,5-di-O-acetyl-3-(1,2,4-triazol-1-yl)-2,3,6-trideoxy-L-arabino-hexofuranose
• 英文别名: [(4S,5R)-5-[(1S)-1-acetyloxyethyl]-4-(1,2,4-triazol-1-yl)oxolan-2-yl] acetate
• CAS: 142137-99-3；142138-00-9
• 化学式: C₁₂H₁₇N₃O₅
• 分子量: 283.284
• InChiKey: VISVYWHNYZFKRK-AOOJPWCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  92.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,5-di-O-acetyl-3-(1,2,4-triazol-1-yl)-2,3,6-trideoxy-L-arabino-hexofuranose 在 三氟甲磺酸三甲基硅酯 、 甲胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 26.0h， 生成 1-(3-(1,2,4-triazol-1-yl)-2,3,6-trideoxy-β-L-arabino-hexofuranosyl)uracil
  参考文献：
  名称：

  Synthesis of 1-(3-(1,2,4-triazol-1-yl)-2,3,6-trideoxy-L-arabino-hexofuranosyl)uracils via an ?,?-unsaturated aldehydrohexose

  摘要：

  Mercuric catalyzed hydrolysis of acetylated L-rhamnal 1 gave the alpha,beta-unsaturated aldehyde 2. 1,2,4-Triazole was coupled, in a Michael type addition reaction, to 2 at C-3 in the presence of 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU) to give, after acetylation at the anomeric center, an anomeric mixture of 1,5-di-O-acetyl-3-(1,2,4-triazol-1-yl)-2,3,6-trideoxy-L-arabino-hexofuranose (3). Reaction of 3 with silylated 2,4-dihydroxypyrimidines 4 in the presence of trimethylsilyl triflate as catalyst followed by deprotection with 33% methylamine in absolute ethanol afforded the corresponding nucleosides 7 and 8.

  DOI：

  10.1007/bf00810947
• 作为产物：
  描述：

  (E)-4-O-acetyl-2,3,6-trideoxy-aldehydo-L-erythro-hex-2-enose 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1,5-di-O-acetyl-3-(1,2,4-triazol-1-yl)-2,3,6-trideoxy-L-arabino-hexofuranose
  参考文献：
  名称：

  Synthesis of 1-(3-(1,2,4-triazol-1-yl)-2,3,6-trideoxy-L-arabino-hexofuranosyl)uracils via an ?,?-unsaturated aldehydrohexose

  摘要：

  Mercuric catalyzed hydrolysis of acetylated L-rhamnal 1 gave the alpha,beta-unsaturated aldehyde 2. 1,2,4-Triazole was coupled, in a Michael type addition reaction, to 2 at C-3 in the presence of 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU) to give, after acetylation at the anomeric center, an anomeric mixture of 1,5-di-O-acetyl-3-(1,2,4-triazol-1-yl)-2,3,6-trideoxy-L-arabino-hexofuranose (3). Reaction of 3 with silylated 2,4-dihydroxypyrimidines 4 in the presence of trimethylsilyl triflate as catalyst followed by deprotection with 33% methylamine in absolute ethanol afforded the corresponding nucleosides 7 and 8.

  DOI：

  10.1007/bf00810947