8-azidooctyl 2,3-di-O-benzoyl-5-O-(tert-butyldiphenylsilyl)-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-D-arabinofuranoside | 950597-92-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-azidooctyl 2,3-di-O-benzoyl-5-O-(tert-butyldiphenylsilyl)-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-D-arabinofuranoside
• CAS: 950597-92-9
• 化学式: C₈₁H₈₃N₃O₁₉Si
• 分子量: 1430.64
• InChiKey: CXDPPZIJNKENGF-DPIYQVIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.79
• 重原子数：
  104.0
• 可旋转键数：
  33.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  271.17
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  8-azidooctyl 2,3-di-O-benzoyl-5-O-(tert-butyldiphenylsilyl)-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-D-arabinofuranoside 在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到8-azidooctyl 2,3-di-O-benzoyl-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of the Docosanasaccharide Arabinan Domain of Mycobacterial Arabinogalactan and a Proposed Octadecasaccharide Biosynthetic Precursor

  摘要：

  Two major components of the cell wall in mycobacteria, including Mycobacterium tuberculosis, the causative agent of tuberculosis (TB), are polysaccharides containing arabinofuranose residues. In one of these polysaccharides, arabinogalactan, this arabinan domain consists of three identical motifs of 22 arabinofuranose residues, which are in turn attached to an underlying galactofuranan backbone. Recent studies have proposed that this docosanasaccharide motif, and a structurally related arabinan present in another cell wall polysaccharide, lipoarabinomannan, are biosynthesized from a common octadecasaccharide precursor. To facilitate the testing of this hypothesis, we report here the first total syntheses of these 18- and 22-residue oligosaccharides both functionalized with an aminooctyl linker arm. The route to the target compounds involved the preparation of four tri- to heptasaccharide building blocks possessing only benzoyl protecting groups that were coupled in a highly convergent manner via glycosyl trichloroacetimidate donors. Each of the targets could be prepared in only six steps from these intermediates, and in both cases more than 10 mg of material was obtained. These compounds are expected to be useful tools in probing the biosynthesis of these arabinan-containing polysaccharides. Such studies are essential prerequisites for the identification of novel anti-TB agents that target arabinan assembly.

  DOI：

  10.1021/ja072892+
• 作为产物：
  描述：

  p-tolyl 2,3-di-O-benzoyl-5-O-(tert-butyldiphenylsilyl)-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-1-thio-α-D-arabinofuranoside 、 8-azidooctyl 2,3-di-O-benzoyl-5-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以84%的产率得到8-azidooctyl 2,3-di-O-benzoyl-5-O-(tert-butyldiphenylsilyl)-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of the Docosanasaccharide Arabinan Domain of Mycobacterial Arabinogalactan and a Proposed Octadecasaccharide Biosynthetic Precursor

  摘要：

  Two major components of the cell wall in mycobacteria, including Mycobacterium tuberculosis, the causative agent of tuberculosis (TB), are polysaccharides containing arabinofuranose residues. In one of these polysaccharides, arabinogalactan, this arabinan domain consists of three identical motifs of 22 arabinofuranose residues, which are in turn attached to an underlying galactofuranan backbone. Recent studies have proposed that this docosanasaccharide motif, and a structurally related arabinan present in another cell wall polysaccharide, lipoarabinomannan, are biosynthesized from a common octadecasaccharide precursor. To facilitate the testing of this hypothesis, we report here the first total syntheses of these 18- and 22-residue oligosaccharides both functionalized with an aminooctyl linker arm. The route to the target compounds involved the preparation of four tri- to heptasaccharide building blocks possessing only benzoyl protecting groups that were coupled in a highly convergent manner via glycosyl trichloroacetimidate donors. Each of the targets could be prepared in only six steps from these intermediates, and in both cases more than 10 mg of material was obtained. These compounds are expected to be useful tools in probing the biosynthesis of these arabinan-containing polysaccharides. Such studies are essential prerequisites for the identification of novel anti-TB agents that target arabinan assembly.

  DOI：

  10.1021/ja072892+