1-O-methyl-6-O-[(3S)-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)-2-methylenebutanoyl]-2,3,4-tri-O-trimethylsilyl-α-D-glucopyranose | 1222854-41-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 1-O-methyl-6-O-[(3S)-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)-2-methylenebutanoyl]-2,3,4-tri-O-trimethylsilyl-α-D-glucopyranose
• CAS: 1222854-41-2
• 化学式: C₃₅H₆₆O₁₀Si₄
• 分子量: 759.245
• InChiKey: KVUATGAWFLWXHP-FCOUXFCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.73
• 重原子数：
  49.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  100.14
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-O-methyl-6-O-[(3S)-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)-2-methylenebutanoyl]-2,3,4-tri-O-trimethylsilyl-α-D-glucopyranose 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到(3’S)-6-O-(3’,4’-dihydroxy-2’-methylenebutanoyl)-1-O-methyl-α-D-glucopyranoside
  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：

  methyl 2,3,4-tri-O-trimethylsilyl-α-D-glucopyranoside 、 3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)-2-methylenebutanoic acid 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到1-O-methyl-6-O-[(3S)-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)-2-methylenebutanoyl]-2,3,4-tri-O-trimethylsilyl-α-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