methyl 2-O-benzyl-3,5-di-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside | 402759-09-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-benzyl-3,5-di-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside
• 英文别名: methyl 3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->3)-[3,5-di-O-benzyl-α-D-arabinofuranosyl-(1->5)]-2-O-benzyl-α-D-arabinofuranoside；Bn(-3)[Bn(-5)]D-Araf(a1-3)[Bn(-3)[Bn(-5)]D-Araf(a1-5)][Bn(-2)]a-D-Araf1Me；(2S,3S,4S,5R)-2-[[(2R,3R,4S,5S)-3-[(2R,3S,4S,5R)-3-hydroxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-2-yl]oxy-5-methoxy-4-phenylmethoxyoxolan-2-yl]methoxy]-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-ol
• CAS: 402759-09-5
• 化学式: C₅₁H₅₈O₁₃
• 分子量: 879.014
• InChiKey: JGZAWXBFEPYHCC-WLBXHYDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  64
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl 2-O-benzyl-3,5-di-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside 在 palladium on activated charcoal N-碘代丁二酰亚胺 、 molecular sieve 、 氢气 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl 3-O-(α-D-arabinofuranosyl)-5-O-(2-O-(β-D-arabinofuranosyl)-α-D-arabonofuranosyl)-α-D-arabinofuranoside
  参考文献：
  名称：

  分枝杆菌的阿拉伯呋喃糖苷：高度分支的六糖及其相关片段的合成，其中包含β-阿拉伯呋喃糖基残基。

  摘要：

  报道了11种含有β-阿拉伯呋喃糖基残基的寡糖（4-14）的合成。聚糖是分枝杆菌细胞壁复合物中发现的两种多糖阿拉伯半乳聚糖和脂质阿拉伯糖甘露聚糖的全部片段。在制备靶标中，关键步骤是低温糖基化反应，该反应安装了具有良好至优异立体控制效果的β-阿拉伯呋喃糖基残基。

  DOI：

  10.1021/jo010910e
• 作为产物：
  描述：

  methyl 3,5-di-O-benzyl-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 molecular sieve 、 三氟化硼乙醚 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 methyl 2-O-benzyl-3,5-di-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside
  参考文献：
  名称：

  分枝杆菌的阿拉伯呋喃糖苷：高度分支的六糖及其相关片段的合成，其中包含β-阿拉伯呋喃糖基残基。

  摘要：

  报道了11种含有β-阿拉伯呋喃糖基残基的寡糖（4-14）的合成。聚糖是分枝杆菌细胞壁复合物中发现的两种多糖阿拉伯半乳聚糖和脂质阿拉伯糖甘露聚糖的全部片段。在制备靶标中，关键步骤是低温糖基化反应，该反应安装了具有良好至优异立体控制效果的β-阿拉伯呋喃糖基残基。

  DOI：

  10.1021/jo010910e

文献信息

• β-Selective Arabinofuranosylation Using a 2,3-<i>O</i>-Xylylene-Protected Donor
  作者：Akihiro Imamura、Todd L. Lowary

  DOI：10.1021/ol101520q

  日期：2010.8.20

  Reported is a novel stereoselective beta-arabinofuranosylation that makes use of a conformationally restricted 2,3-O-zylylene-protected arabinofuranosyl donor. Optimization of the reaction conditions showed that factors including the structure of the acceptor alcohol, substrate concentration, and protecting group on O-5 of the donor affect the stereochemical outcome of the glycosylation. To demonstrate the utility of the methodology, the synthesis of an oligosaccharide fragment from the mycobacterial cell wall polysaccharide lipoarabinomannan was carried out.
• Ligand Specificity of CS-35, a Monoclonal Antibody That Recognizes Mycobacterial Lipoarabinomannan:  A Model System for Oligofuranoside−Protein Recognition
  作者：Christoph Rademacher、Glen K. Shoemaker、Hyo-Sun Kim、Ruixiang Blake Zheng、Hashem Taha、Chunjuan Liu、Ruel C. Nacario、David C. Schriemer、John S. Klassen、Thomas Peters、Todd L. Lowary

  DOI：10.1021/ja0723380

  日期：2007.8.1

  The CS-35 antibody is widely used in the characterization of glycans containing D-arabinofuranose residues, in particular polysaccharides present in the mycobacterial cell wall. A detailed understanding of the combining site of this antibody and the measurement of its binding to different ligands is of interest as this knowledge will have implications in the characterization of arabinofuranose-containing glycoconjugates that are increasingly recognized as important biological molecules. Of even greater significance is that an in-depth study of this carbohydrate-protein interaction will provide insights into the mechanisms by which oligosaccharides containing furanose rings are bound by proteins, an area that has, to date, received little attention. This system has been refractory to X-ray crystallography, and thus we report here a study of the interaction of CS-35 with its ligands using a combination of chemical synthesis, mass spectrometry, titration microcalorimetry, and NMR spectroscopy. Through these investigations we have established that the binding pocket recognizes, as a minimum epitope, a linear tetrasaccharide motif and that the residues at the reducing and non-reducing end of the oligosaccharide are essential for tight binding. The residue at the non-reducing end appears to be bound in an aliphatic pocket, whereas the rest of the tetrasaccharide interacts more strongly with aromatic amino acids.
• Arabinofuranosides from Mycobacteria:  Synthesis of a Highly Branched Hexasaccharide and Related Fragments Containing β-Arabinofuranosyl Residues
  作者：Haifeng Yin、Francis W. D'Souz、Todd L. Lowary

  DOI：10.1021/jo010910e

  日期：2002.2.1

  The synthesis of 11 oligosaccharides (4-14) containing beta-arabinofuranosyl residues is reported. The glycans are all fragments of two polysaccharides, arabinogalactan and lipoarabinomannan, which are found in the cell wall complex of mycobacteria. In the preparation of the targets, the key step was a low-temperature glycosylation reaction that installed the beta-arabinofuranosyl residues with good

  报道了11种含有β-阿拉伯呋喃糖基残基的寡糖（4-14）的合成。聚糖是分枝杆菌细胞壁复合物中发现的两种多糖阿拉伯半乳聚糖和脂质阿拉伯糖甘露聚糖的全部片段。在制备靶标中，关键步骤是低温糖基化反应，该反应安装了具有良好至优异立体控制效果的β-阿拉伯呋喃糖基残基。