N-({1-[ethyl 2,3-di-O-acetyl-6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-mannopyranosid-4-yl]-1H-1,2,3-triazol-4-yl}methyl)-3-(3-phenyl-1,2,4-oxadiazol-5-yl)propanamide | 1051378-39-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-({1-[ethyl 2,3-di-O-acetyl-6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-mannopyranosid-4-yl]-1H-1,2,3-triazol-4-yl}methyl)-3-(3-phenyl-1,2,4-oxadiazol-5-yl)propanamide
• 英文别名: [(2S,3R,4S,5S,6S)-5-acetyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-ethoxy-3-[4-[[3-(3-phenyl-1,2,4-oxadiazol-5-yl)propanoylamino]methyl]triazol-1-yl]oxan-4-yl] acetate
• CAS: 1051378-39-2
• 化学式: C₃₂H₄₆N₆O₉Si
• 分子量: 686.838
• InChiKey: ZREQEZKWNDUWLJ-AWTCAUSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  、 乙酸酐 在 吡啶 作用下， 反应 24.0h， 生成 N-({1-[ethyl 2,3-di-O-acetyl-6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-mannopyranosid-4-yl]-1H-1,2,3-triazol-4-yl}methyl)-3-(3-phenyl-1,2,4-oxadiazol-5-yl)propanamide
  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