{1-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-1H-1,2,3-triazol-4-yl}methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 1051378-28-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: {1-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-1H-1,2,3-triazol-4-yl}methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-[[1-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]triazol-4-yl]methoxy]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1051378-28-9
• 化学式: C₂₂H₂₃N₅O₇
• 分子量: 469.454
• InChiKey: QTQPZSMAOPEPKP-HBMCJLEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  {1-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-1H-1,2,3-triazol-4-yl}methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 potassium osmate(VI) 、 N-甲基吲哚酮 、 柠檬酸 作用下， 以 水 、 叔丁醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Some Unusual (1,2,4-Oxadiazole)-Linked Hexenopyranosides and Mannopyranosides

  摘要：

  A copper-catalyzed reaction of propargyl 4,6-di-O-acetyl-2,3-dideoxy-alpha-D-erythro-hex-2-enopyranoside with 3-(4-azidophenyl)-1,2,4-oxadiazoles gave the corresponding hexenopyranosides bearing an 1,2,4-oxadiazole subunit in the aglyconic part of the molecule. The same reaction between ethyl 4-azido-2,3,4-trideoxy-alpha-D-erythro-hex-2-enopyranoside and acetylenic 1,2,4-oxadiazoles afforded the corresponding hexenopyranosides carrying a triazole and a 1,2,4-oxadiazole ring at C-4 of the carbohydrate. Combination of the two sequences gave hexenopyranosides displaying two 1,2,4-oxadiazole subunits, each one being embedded in the C-1 and C-4 frameworks, of the carbohydrate moiety. A simple dihydroxylation reaction of these unsaturated carbohydrates yielded a series of mannopyranosides bearing one or two 1,2,4-oxadiazole subunits at C-1 or C-4. These new compounds were evaluated for their cytotoxic activities against two cell strains: NCI-H-292 (lung carcinoma) and Hep-2 (larynx carcinoma), some of them presenting impressive cell growth inhibitions.

  DOI：

  10.1080/07328300802120901
• 作为产物：
  描述：

  3-(4-azidophenyl)-5-methyl-1,2,4-oxadiazole 、 2-propynyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 copper diacetate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 23.0h， 以87%的产率得到{1-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-1H-1,2,3-triazol-4-yl}methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Synthesis of Some Unusual (1,2,4-Oxadiazole)-Linked Hexenopyranosides and Mannopyranosides

  摘要：

  A copper-catalyzed reaction of propargyl 4,6-di-O-acetyl-2,3-dideoxy-alpha-D-erythro-hex-2-enopyranoside with 3-(4-azidophenyl)-1,2,4-oxadiazoles gave the corresponding hexenopyranosides bearing an 1,2,4-oxadiazole subunit in the aglyconic part of the molecule. The same reaction between ethyl 4-azido-2,3,4-trideoxy-alpha-D-erythro-hex-2-enopyranoside and acetylenic 1,2,4-oxadiazoles afforded the corresponding hexenopyranosides carrying a triazole and a 1,2,4-oxadiazole ring at C-4 of the carbohydrate. Combination of the two sequences gave hexenopyranosides displaying two 1,2,4-oxadiazole subunits, each one being embedded in the C-1 and C-4 frameworks, of the carbohydrate moiety. A simple dihydroxylation reaction of these unsaturated carbohydrates yielded a series of mannopyranosides bearing one or two 1,2,4-oxadiazole subunits at C-1 or C-4. These new compounds were evaluated for their cytotoxic activities against two cell strains: NCI-H-292 (lung carcinoma) and Hep-2 (larynx carcinoma), some of them presenting impressive cell growth inhibitions.

  DOI：

  10.1080/07328300802120901