N-({1-[ethyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl]-1H-1,2,3-triazol-4-yl}methyl)-3-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl]propanamide | 1051378-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-({1-[ethyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl]-1H-1,2,3-triazol-4-yl}methyl)-3-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl]propanamide
• 英文别名: 3-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl]-N-[[1-[(2S,3S,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-ethoxy-3,6-dihydro-2H-pyran-3-yl]triazol-4-yl]methyl]propanamide
• CAS: 1051378-31-4
• 化学式: C₂₈H₃₉BrN₆O₅Si
• 分子量: 647.644
• InChiKey: GFTWXRBNTSUQCE-ZEVJAHDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-({1-[ethyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl]-1H-1,2,3-triazol-4-yl}methyl)-3-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl]propanamide 在 四氧化锇 、 N-甲基吲哚酮 、 水 作用下， 以 丙酮 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：

  ethyl 4-azido-6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranoside 、 3-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl]-N-(prop-2-yn-1-yl)propanamide 在 copper diacetate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 17.0h， 以77%的产率得到N-({1-[ethyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranosid-4-yl]-1H-1,2,3-triazol-4-yl}methyl)-3-[3-(4-bromophenyl)-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