phenyl (3-azido-2,3-dideoxy-4-trimethylsilyl-α-L-fucopyranosyl)-(1-4)-3-azido-2,3-dideoxy-1-thio-α-L-fucopyranoside | 264626-91-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl (3-azido-2,3-dideoxy-4-trimethylsilyl-α-L-fucopyranosyl)-(1-4)-3-azido-2,3-dideoxy-1-thio-α-L-fucopyranoside
• CAS: 264626-91-7
• 化学式: C₂₁H₃₂N₆O₄SSi
• 分子量: 492.674
• InChiKey: AUAFUAXOJQWKOK-XGCSAWHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  134.44
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  phenyl (3-azido-2,3-dideoxy-4-trimethylsilyl-α-L-fucopyranosyl)-(1-4)-3-azido-2,3-dideoxy-1-thio-α-L-fucopyranoside 在 三氟甲磺酸酐 、 4 A molecular sieve 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 phenyl [[[[(3-azido-2,3-dideoxy-4-trimethylsilyl-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-3-azido-2,3-dideoxy-1-thio-α-...
  参考文献：
  名称：

  Design of an Oligosaccharide Scaffold That Binds in the Minor Groove of DNA

  摘要：

  Many biological recognition events involve extensive interactions between macromolecules. Strategies to design compounds that mimic large peptides or other elements of secondary structure could be useful for blocking interactions between large surfaces. In this paper, the use of oligosaccharides as scaffolds for the design of peptidomimetics is addressed. A functionalized oligosaccharide modeled after a basic region peptide helix has been designed and synthesized. This oligosaccharide binds to duplex DNA with micromolar affinity. The mode of binding has been established by 2D NMR, and shows that the oligosaccharide binds DNA in the minor groove with one surface of the oligosaccharide contacting the floor of the DNA.

  DOI：

  10.1021/ja992513f
• 作为产物：
  描述：

  (2S,3S,4S,6S)-4-azido-2-methyl-6-phenylsulfanyloxan-3-ol 、 ((2S,3S,4S)-4-Azido-6-benzenesulfinyl-2-methyl-tetrahydro-pyran-3-yloxy)-trimethyl-silane 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.25h， 以44%的产率得到phenyl (3-azido-2,3-dideoxy-4-trimethylsilyl-α-L-fucopyranosyl)-(1-4)-3-azido-2,3-dideoxy-1-thio-α-L-fucopyranoside
  参考文献：
  名称：

  Design of an Oligosaccharide Scaffold That Binds in the Minor Groove of DNA

  摘要：

  Many biological recognition events involve extensive interactions between macromolecules. Strategies to design compounds that mimic large peptides or other elements of secondary structure could be useful for blocking interactions between large surfaces. In this paper, the use of oligosaccharides as scaffolds for the design of peptidomimetics is addressed. A functionalized oligosaccharide modeled after a basic region peptide helix has been designed and synthesized. This oligosaccharide binds to duplex DNA with micromolar affinity. The mode of binding has been established by 2D NMR, and shows that the oligosaccharide binds DNA in the minor groove with one surface of the oligosaccharide contacting the floor of the DNA.

  DOI：

  10.1021/ja992513f