4,5-di(methoxycarbonyl)-1-(ethyl 6-O-acetyl-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl)-1H-1,2,3-triazole | 914795-42-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-di(methoxycarbonyl)-1-(ethyl 6-O-acetyl-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl)-1H-1,2,3-triazole
• 英文别名: dimethyl 1-[(2S,3S,6S)-2-(acetyloxymethyl)-6-ethoxy-3,6-dihydro-2H-pyran-3-yl]triazole-4,5-dicarboxylate
• CAS: 914795-42-9
• 化学式: C₁₆H₂₁N₃O₈
• 分子量: 383.358
• InChiKey: GDBSIXZCOZQWBJ-TUAOUCFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4,5-di(methoxycarbonyl)-1-(ethyl 6-O-acetyl-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl)-1H-1,2,3-triazole 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 为溶剂， 生成 1-((2S,3S,4S,5S,6S)-2-Acetoxymethyl-6-ethoxy-4,5-dihydroxy-tetrahydro-pyran-3-yl)-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Efficient Synthesis of Some Unsaturated [1,2,3]‐Triazole‐Linked Glycoconjugates

  摘要：

  Thermal 1,3-dipolar cycloaddition of ethyl 4-azido-2,3,4-trideoxy-alpha-D- erythro -hex-2-enopyranosides with diethyl acetylenedicarboxylate or copper-catalyzed reaction with various functionalized alkynes gave the corresponding 1-(ethyl 2,3,4-trideoxy-alpha-D- erythro -hex-2-enopyranosid-4-yl)-1 H -1,2,3-triazole derivatives in quite good yields. These unsaturated compounds could be transformed into 1-(ethyl 2,3-di-O-acetyl-4-deoxy-alpha-D-mannopyranosid-4-yl)-1 H -1,2,3-triazoles by a simple dihydroxylation reaction. Copper-catalyzed condensation of ethyl 6-O-acetyl-4-azido-2,3,4-trideoxy-alpha-D- erythro-hex-2-enopyranoside with 1,3,5-triethynylbenzene or 1,3,5-tris(prop-2-ynyloxy)benzene afforded the corresponding trivalent glycoconjugate clusters.

  DOI：

  10.1080/07328300600803484
• 作为产物：
  描述：

  ethyl 6-O-acetyl-4-azido-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranoside 、 丁炔二酸二甲酯 反应 5.0h， 以90%的产率得到4,5-di(methoxycarbonyl)-1-(ethyl 6-O-acetyl-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Efficient Synthesis of Some Unsaturated [1,2,3]‐Triazole‐Linked Glycoconjugates

  摘要：

  Thermal 1,3-dipolar cycloaddition of ethyl 4-azido-2,3,4-trideoxy-alpha-D- erythro -hex-2-enopyranosides with diethyl acetylenedicarboxylate or copper-catalyzed reaction with various functionalized alkynes gave the corresponding 1-(ethyl 2,3,4-trideoxy-alpha-D- erythro -hex-2-enopyranosid-4-yl)-1 H -1,2,3-triazole derivatives in quite good yields. These unsaturated compounds could be transformed into 1-(ethyl 2,3-di-O-acetyl-4-deoxy-alpha-D-mannopyranosid-4-yl)-1 H -1,2,3-triazoles by a simple dihydroxylation reaction. Copper-catalyzed condensation of ethyl 6-O-acetyl-4-azido-2,3,4-trideoxy-alpha-D- erythro-hex-2-enopyranoside with 1,3,5-triethynylbenzene or 1,3,5-tris(prop-2-ynyloxy)benzene afforded the corresponding trivalent glycoconjugate clusters.

  DOI：

  10.1080/07328300600803484