ethyl 2,3-di-O-acetyl-6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-4-{4-[4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl]-1H-1,2,3-triazol-4-yl}-α-D-mannopyranoside | 1051378-38-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3-di-O-acetyl-6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-4-{4-[4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl]-1H-1,2,3-triazol-4-yl}-α-D-mannopyranoside
• CAS: 1051378-38-1
• 化学式: C₃₄H₄₃N₅O₈Si
• 分子量: 677.83
• InChiKey: IJZGFANHTJWEKA-XZEPXJLQSA-N

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 ethyl 2,3-di-O-acetyl-6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-4-{4-[4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl]-1H-1,2,3-triazol-4-yl}-α-D-mannopyranoside
  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