1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranose | 796873-39-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranose
• CAS: 796873-39-7
• 化学式: C₁₉H₂₃N₃O₁₀
• 分子量: 453.406
• InChiKey: XOQJWTNPXRCKDM-CXQDZFQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.72
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  192.9
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranose 在 palladium dihydroxide 吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 氢气 、 硼酸 、 potassium carbonate 、 苄胺 、 三氟乙酸 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 103.5h， 生成 methyl 2-acetamido-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of disaccharides derived from heparin and evaluation of effects on endothelial cell growth and on binding of heparin to FGF-2

  摘要：

  The disaccharide beta-D-GlcA-(1 --> 4)-alpha-D-GlcNAc-1 --> OMe and other small nonsulfated oligosaccharides related to heparin/heparan sulfate have been shown to bind to FGF and activated the fibroblast growth factor (FGF) signalling pathway in (F32) cells expressing the FGF receptor. Synthetic routes to beta-D-GlcA-(1 --> 4)-alpha-D-GlcNAc-1 --> OMe and a glucose analogue beta-D-Glc(1 --> 4)-alpha-D-GlcNAc-1 --> OMe are described. The effects of these disaccharides on endothelial cell growth, which is relevant to angiogenesis, were evaluated and it was found they did not mimic the inhibitory effects that were observed for heparin albumin (HA) and that have also been observed by monosaccharide conjugates. They did not alter bovine aortic endothelial cell (BAEC) proliferation, in the presence of FGF-2 in serum free medium or in absence of FGF-2 in serum free and complete medium. Disaccharides (10 mug/mL) reduced by 25-31% the inhibition caused by HA (10 mug/mL) on BAEC growth in serum-free medium but had no effect in complete medium. There was no evidence obtained for the binding of these oligosaccharides to FGF-2 in competition with HA by ELISA. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.07.018
• 作为产物：
  描述：

  1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-β-D-glucopyranose 在 sodium hypochlorite 、 1,2,6,6-tetramethylpiperidine-1-oxide 、 sodium methylate 、 potassium bromide 作用下， 以 四氢呋喃 、 甲醇 、 碳酸氢钠 为溶剂， 反应 48.5h， 生成 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of disaccharides derived from heparin and evaluation of effects on endothelial cell growth and on binding of heparin to FGF-2

  摘要：

  The disaccharide beta-D-GlcA-(1 --> 4)-alpha-D-GlcNAc-1 --> OMe and other small nonsulfated oligosaccharides related to heparin/heparan sulfate have been shown to bind to FGF and activated the fibroblast growth factor (FGF) signalling pathway in (F32) cells expressing the FGF receptor. Synthetic routes to beta-D-GlcA-(1 --> 4)-alpha-D-GlcNAc-1 --> OMe and a glucose analogue beta-D-Glc(1 --> 4)-alpha-D-GlcNAc-1 --> OMe are described. The effects of these disaccharides on endothelial cell growth, which is relevant to angiogenesis, were evaluated and it was found they did not mimic the inhibitory effects that were observed for heparin albumin (HA) and that have also been observed by monosaccharide conjugates. They did not alter bovine aortic endothelial cell (BAEC) proliferation, in the presence of FGF-2 in serum free medium or in absence of FGF-2 in serum free and complete medium. Disaccharides (10 mug/mL) reduced by 25-31% the inhibition caused by HA (10 mug/mL) on BAEC growth in serum-free medium but had no effect in complete medium. There was no evidence obtained for the binding of these oligosaccharides to FGF-2 in competition with HA by ELISA. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.07.018

文献信息

• Glycosidation–Anomerisation Reactions of 6,1-Anhydroglucopyranuronic Acid and Anomerisation of β-D-Glucopyranosiduronic Acids Promoted by SnCl4
  作者：Colin O'Brien、Monika Poláková、Nigel Pitt、Manuela Tosin、Paul V. Murphy

  DOI：10.1002/chem.200601111

  日期：2007.1.12

  onic acids was found to be faster, in some cases, than anomerisation of related beta-D-glucopyranosiduronic acid esters and beta-D-glucopyranoside derivatives and the rates are dependent on the structure of the aglycon. Moreover, the rates of anomerisation of beta-D-glucopyranuronic acid derivatives can be qualitatively correlated with rates of hydrolysis of beta-D-glucopyranosiduronic acids. Mechanistic

  氯化锡（IV）催化的甲硅烷基化亲核试剂与6,1-脱水葡萄糖基吡喃糖醛酸（葡萄糖醛酸6,1-内酯）的反应提供了1,2-反式或1,2-顺式（脱氧）糖苷，具体取决于供体结构。对于供体与2-酰基和2-脱氧供体的反应，获得了α-糖苷，而2-脱氧-2-碘的供体给出了β-糖苷。实验证据表明，当1,2-顺式糖苷形成时，由SnCl（4）催化的最初形成的1,2-反式糖苷的异构化是可能的。在某些情况下，发现β-D-吡喃葡萄糖苷神经酸酯的异构化比相关的β-D-吡喃葡萄糖苷神经酸酯和β-D-吡喃葡萄糖苷衍生物的异构化更快，并且速率取决于糖苷配基的结构。而且，β-D-吡喃葡萄糖醛酸衍生物的异构化速率可以与β-D-吡喃葡萄糖醛糖醛酸的水解速率定性相关。考虑了反应的机械可能性。