6-O-(p-toluenesulfonyl)-1-O-(2-trimethylsilylethyl)-β-D-glucopyranose | 1222854-26-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(p-toluenesulfonyl)-1-O-(2-trimethylsilylethyl)-β-D-glucopyranose
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-trimethylsilylethoxy)oxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 1222854-26-3
• 化学式: C₁₈H₃₀O₈SSi
• 分子量: 434.583
• InChiKey: LZSXXQXOZKTLFH-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-O-(p-toluenesulfonyl)-1-O-(2-trimethylsilylethyl)-β-D-glucopyranose 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以92%的产率得到6-azido-6-deoxy-1-O-(2-trimethylsilylethyl)-β-D-glucopyranose
  参考文献：
  名称：

  The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure–activity relationship

  摘要：

  6-Tuliposide B is a secondary metabolite occurring specifically in tulip anthers. Recently, a potent antibacterial activity of 6-tuliposide B has been reported. However, its molecular target has not yet been established, nor its action mechanism. To shed light on such issues, 6-tuliposide B and tulipalin B analogues were synthesized and a structure-activity relationship (SAR) was examined using a broad panel of bacterial strains. As the results of SAR among a total of 25 compounds, only tulipalin B and the compounds having 3',4'-dihydroxy-2'-methylenebutanoate (DHMB) moieties showed any significant antibacterial activity. Moreover, the 3'R analogues of these compounds displayed essentially the same activities as 6-tuliposide B and the structure of the 3'R-DMBA moiety was the same as that of the proposed active moiety of cnicin. These results suggest that 6-tuliposide B has the same action mechanism as proposed for cnicin and bacteria) MurA is one of the major molecular targets of 6-tuliposide B. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.10.008
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl β-D-glucopyranoside 、 对甲苯磺酰氯 在 吡啶 作用下， 以83%的产率得到6-O-(p-toluenesulfonyl)-1-O-(2-trimethylsilylethyl)-β-D-glucopyranose
  参考文献：
  名称：

  The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure–activity relationship

  摘要：

  6-Tuliposide B is a secondary metabolite occurring specifically in tulip anthers. Recently, a potent antibacterial activity of 6-tuliposide B has been reported. However, its molecular target has not yet been established, nor its action mechanism. To shed light on such issues, 6-tuliposide B and tulipalin B analogues were synthesized and a structure-activity relationship (SAR) was examined using a broad panel of bacterial strains. As the results of SAR among a total of 25 compounds, only tulipalin B and the compounds having 3',4'-dihydroxy-2'-methylenebutanoate (DHMB) moieties showed any significant antibacterial activity. Moreover, the 3'R analogues of these compounds displayed essentially the same activities as 6-tuliposide B and the structure of the 3'R-DMBA moiety was the same as that of the proposed active moiety of cnicin. These results suggest that 6-tuliposide B has the same action mechanism as proposed for cnicin and bacteria) MurA is one of the major molecular targets of 6-tuliposide B. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.10.008