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 | 950597-91-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• CAS: 950597-91-8
• 化学式: C₆₁H₅₈O₁₂SSi
• 分子量: 1043.28
• InChiKey: NWXRFLTVCYIUQH-NVVLVVJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.03
• 重原子数：
  75.0
• 可旋转键数：
  18.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  142.12
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  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-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-D-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-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86%的产率得到
  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-toluyl 2,3-di-O-benzoyl-1-thio-α-D-arabinofuranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以0.67 g的产率得到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
  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+

文献信息

• Development of an Orthogonal Protection Strategy for the Synthesis of Mycobacterial Arabinomannan Fragments
  作者：Kamar Sahloul、Todd L. Lowary

  DOI：10.1021/acs.joc.5b02083

  日期：2015.11.20

  Mycobacterium tuberculosis, the organism that causes tuberculosis (TB), has a carbohydrate-rich cell wall structure that possesses a number of immunogenic antigens. Circulating antibodies that recognize these glycans are present in patients infected by mycobacteria; detection of these antibodies could be the basis for new TB diagnostics. We describe here the synthesis of a panel of mycobacterial arabinomannan

  结核分枝杆菌是导致结核病（TB）的生物，具有富含碳水化合物的细胞壁结构，该结构具有许多免疫原性抗原。分枝杆菌感染的患者中存在识别这些聚糖的循环抗体。这些抗体的检测可能是新的结核病诊断的基础。我们在这里描述了一组分枝杆菌阿拉伯甘露聚糖片段的合成，以用于针对测试这种诊断方法的可行性的研究。在这项研究中，我们重点研究了关键免疫原性多糖脂阿拉伯糖甘露聚糖（LAM）核心中存在的结构基序。为了获得这些化合物，我们开发了一种有效的正交保护策略，该策略可以访问LAM的七个阿拉伯甘露聚糖片段（1 – 7）。靶标包括一种四糖，一种五糖，三种八糖和两种九糖。从受不同保护的三甘露吡喃糖苷衍生物（8或9）开始，采用以下方法获得靶标，该方法包括选择性去除单个甘露吡喃糖苷残基O-2位置上存在的保护基，然后用戊阿拉伯呋喃糖硫糖苷和/或甘露吡喃糖三氯乙酰亚胺。