2,3-di-O-benzyl-β-D-arabinofuranosyl-(1f2)-3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose | 1268604-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-di-O-benzyl-β-D-arabinofuranosyl-(1f2)-3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose
• CAS: 1268604-12-1
• 化学式: C₅₃H₆₀O₁₃
• 分子量: 905.052
• InChiKey: WPRULUFRBBILSA-FWGZSWLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.27
• 重原子数：
  66.0
• 可旋转键数：
  22.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  130.99
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzyl-β-D-arabinofuranosyl-(1f2)-3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose 、 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→5)-2,3-di-O-benzyl-β-D-arabinofuranosyl-(1→2)-3,5-di-O-benzyl-α-D-arabinofuranosyl-(1→5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose
  参考文献：
  名称：

  Synthetic and Immunological Studies of Mycobacterial Lipoarabinomannan Oligosaccharides and Their Protein Conjugates

  摘要：

  Lipoarabinomannan (LAM) is one of the major constituents of the Mycobacterium tuberculosis cell wall and an attractive molecular scaffold for antituberculosis drug and vaccine development. In this paper, a convergent strategy was developed for the synthesis of LAM oligosaccharides with an alpha-1,2-linked dimannopyranose cap at the nonreducing end. The strategy was highlighted by efficient coupling of separately prepared nonreducing end and reducing end oligosaccharides. Glycosylations were mainly achieved with thioglycoside donors, which gave excellent yields and stereoselectivity even for reactions between complex oligosaccharides. The strategy was utilized to successfully synthesize tetra-, hepta-, and undecasaccharides of LAM from D-arabinose in 10, 15, and 14 longest linear steps and 7.84, 7.50, and 2.59% overall yields, respectively. The resultant oligosaccharides with a free amino group at their reducing end were effectively conjugated with carrier proteins, including bovine serum albumin and keyhole limpet hemocyanin (KLH), via a bifunctional linker. Preliminary immunological studies on the KLH conjugates revealed that they could elicit robust antibody responses in mice and that the antigen structure had some influence on their immunological property, thus verifying the potential of the oligosaccharides for vaccine development and other immunological studies.

  DOI：

  10.1021/acs.joc.5b01686
• 作为产物：
  描述：

  p-tolyl 2-O-acetyl-3,5-di-O-benzyl-1-thio-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 四丁基氟化铵 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 2,3-di-O-benzyl-β-D-arabinofuranosyl-(1f2)-3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->5)-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose
  参考文献：
  名称：

  Synthetic and Immunological Studies of Mycobacterial Lipoarabinomannan Oligosaccharides and Their Protein Conjugates

  摘要：

  Lipoarabinomannan (LAM) is one of the major constituents of the Mycobacterium tuberculosis cell wall and an attractive molecular scaffold for antituberculosis drug and vaccine development. In this paper, a convergent strategy was developed for the synthesis of LAM oligosaccharides with an alpha-1,2-linked dimannopyranose cap at the nonreducing end. The strategy was highlighted by efficient coupling of separately prepared nonreducing end and reducing end oligosaccharides. Glycosylations were mainly achieved with thioglycoside donors, which gave excellent yields and stereoselectivity even for reactions between complex oligosaccharides. The strategy was utilized to successfully synthesize tetra-, hepta-, and undecasaccharides of LAM from D-arabinose in 10, 15, and 14 longest linear steps and 7.84, 7.50, and 2.59% overall yields, respectively. The resultant oligosaccharides with a free amino group at their reducing end were effectively conjugated with carrier proteins, including bovine serum albumin and keyhole limpet hemocyanin (KLH), via a bifunctional linker. Preliminary immunological studies on the KLH conjugates revealed that they could elicit robust antibody responses in mice and that the antigen structure had some influence on their immunological property, thus verifying the potential of the oligosaccharides for vaccine development and other immunological studies.

  DOI：

  10.1021/acs.joc.5b01686

文献信息

• Synthesis of Docosasaccharide Arabinan Motif of Mycobacterial Cell Wall
  作者：Akihiro Ishiwata、Yukishige Ito

  DOI：10.1021/ja109932t

  日期：2011.2.23

  Mycobacterial arabinan is a common constituent of both arabinogalactan (AG) and lipoarabinomannan (LAM). In this study, synthesis of β-Araf containing common arabinan docosasaccharide motif (22 Araf monomer units) of mycobacterial cell wall was achieved. Our synthetic strategy toward arabinan involves (1) the stereoselective β-arabinofuranosylation using both 3,5-O-TIPDS-protected and NAP-protected

  分枝杆菌阿拉伯聚糖是阿拉伯半乳聚糖 (AG) 和脂阿拉伯甘露聚糖 (LAM) 的常见成分。在这项研究中，合成了含有常见阿拉伯二十二糖基序（22 个 Araf 单体单元）的分枝杆菌细胞壁的 β-Araf。我们对阿拉伯聚糖的合成策略包括 (1) 立体选择性 β-阿拉伯呋喃糖基化，分别使用 3,5-O-TIPDS 保护和 NAP 保护的阿拉伯呋喃糖基供体进行直接的分子间糖基化和分子内苷元递送 (IAD)，以及 (2)收敛片段与线性序列上的分支片段偶联，使用硫糖苷供体，通过三步程序从每个片段的还原末端相应的丙酮化物获得。