methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosidurono-6,2-lactone | 1415974-09-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosidurono-6,2-lactone
• CAS: 1415974-09-2
• 化学式: C₃₈H₃₉N₃O₁₀
• 分子量: 697.742
• InChiKey: IKZTWNVVPJHGSS-DBVRBXGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  51.0
• 可旋转键数：
  14.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  159.9
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosidurono-6,2-lactone 在 20% palladium hydroxide-activated charcoal 、 氢气 、 三氧化硫-三乙胺复合物 、 lithium hydroxide 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 137.0h， 生成 sodium (methyl 4-O-(2-amino-2-deoxy-6-O-(sodium sulfonato)-α-D-glucopyranosyl)-α-L-idopyranosid)uronate
  参考文献：
  名称：

  Divergent Synthesis of 48 Heparan Sulfate-Based Disaccharides and Probing the Specific Sugar–Fibroblast Growth Factor-1 Interaction

  摘要：

  Several biological processes involve glycans, yet understanding their ligand specificities is impeded by their inherent diversity and difficult acquisition. Generating broad synthetic sugar libraries for bioevaluations is a powerful tool in unraveling glycan structural information. In the case of the widely distributed heparan sulfate (HS), however, the 48 theoretical possibilities for its repeating disaccharide call for synthetic approaches that should minimize the effort in an undoubtedly huge undertaking. Here we employed a divergent strategy to afford all 48 HS-based disaccharides from just two orthogonally protected disaccharide precursors. Different combinations and sequence of transformation steps were applied with many downstream intermediates leading up to multiple target products. With the full disaccharide library in hand, affinity screening with fibroblast growth factor-1 (FGF-1) revealed that four of the synthetic sugars bind to FGF-1. The molecular details of the interaction were further clarified through X-ray analysis of the sugar-protein cocrystals. The capability of comprehensive sugar libraries in providing key insights in glycan-ligand interaction is, thus, highlighted.

  DOI：

  10.1021/ja3090065
• 作为产物：
  描述：

  6-O-acetyl-4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranose 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 三(二甲氨基)锍二氟三甲基硅酸 、 sodium methylate 、 silver trifluoromethanesulfonate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosidurono-6,2-lactone
  参考文献：
  名称：

  Divergent Synthesis of 48 Heparan Sulfate-Based Disaccharides and Probing the Specific Sugar–Fibroblast Growth Factor-1 Interaction

  摘要：

  Several biological processes involve glycans, yet understanding their ligand specificities is impeded by their inherent diversity and difficult acquisition. Generating broad synthetic sugar libraries for bioevaluations is a powerful tool in unraveling glycan structural information. In the case of the widely distributed heparan sulfate (HS), however, the 48 theoretical possibilities for its repeating disaccharide call for synthetic approaches that should minimize the effort in an undoubtedly huge undertaking. Here we employed a divergent strategy to afford all 48 HS-based disaccharides from just two orthogonally protected disaccharide precursors. Different combinations and sequence of transformation steps were applied with many downstream intermediates leading up to multiple target products. With the full disaccharide library in hand, affinity screening with fibroblast growth factor-1 (FGF-1) revealed that four of the synthetic sugars bind to FGF-1. The molecular details of the interaction were further clarified through X-ray analysis of the sugar-protein cocrystals. The capability of comprehensive sugar libraries in providing key insights in glycan-ligand interaction is, thus, highlighted.

  DOI：

  10.1021/ja3090065