6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-methyl-1-O-trichloroacetimidoyl-D-glucopyranose | 241129-78-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-methyl-1-O-trichloroacetimidoyl-D-glucopyranose
• 英文别名: [(2R,3S,4R,5R)-5-azido-3-methoxy-4-phenylmethoxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 241129-78-2
• 化学式: C₁₈H₂₁Cl₃N₄O₆
• 分子量: 495.747
• InChiKey: ZJTZMADUVJZCCC-XIHUBIEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-methyl-1-O-trichloroacetimidoyl-D-glucopyranose 在 叔丁基二甲硅基三氟甲磺酸酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (2R,3S,4S,5R,6R)-5-Acetoxy-3-((2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-6-(2-amino-ethoxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological activity of oligomer-model compounds containing units of a key platelet-binding disaccharide of heparin

  摘要：

  A key disaccharide unit in heparin, O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1-->4)-2-O-sulfo-alpha-L-idopyranosyluronic acid, was previously found to be responsible for the binding interaction of heparin to platelets. A clustering effect to enhance the binding was found to be dependent on the number and frequency of the disaccharide units in a heparin molecule. To systematically examine the clustering effect, three oligomer-model compounds containing two or three units of the disaccharide were synthesized. These compounds inhibited (3)H-Iabelled heparin binding to human platelets more strongly than a compound containing only one unit of the disaccharide, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01084-9
• 作为产物：
  描述：

  在 哌啶 、 caesium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-methyl-1-O-trichloroacetimidoyl-D-glucopyranose
  参考文献：
  名称：

  Synthesis and biological activity of oligomer-model compounds containing units of a key platelet-binding disaccharide of heparin

  摘要：

  A key disaccharide unit in heparin, O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1-->4)-2-O-sulfo-alpha-L-idopyranosyluronic acid, was previously found to be responsible for the binding interaction of heparin to platelets. A clustering effect to enhance the binding was found to be dependent on the number and frequency of the disaccharide units in a heparin molecule. To systematically examine the clustering effect, three oligomer-model compounds containing two or three units of the disaccharide were synthesized. These compounds inhibited (3)H-Iabelled heparin binding to human platelets more strongly than a compound containing only one unit of the disaccharide, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01084-9

文献信息

• Investigating Glycol-Split-Heparin-Derived Inhibitors of Heparanase: A Study of Synthetic Trisaccharides
  作者：Minghong Ni、Stefano Elli、Annamaria Naggi、Marco Guerrini、Giangiacomo Torri、Maurice Petitou

  DOI：10.3390/molecules21111602

  日期：——

  structure glycol-split uronic acid moieties probably responsible for their strong inhibitory activity. We describe here the total chemical synthesis of the trisaccharide GlcNS6S-GlcA-1,6anGlcNS (1) and its glycol-split (gs) counterpart GlcNS6S-gsGlcA-1,6anGlcNS (2) from glucose. As expected, in a heparanase inhibition assay, compound 2 is one order of magnitude more potent than 1. Using molecular modeling

  乙酰肝素酶是唯一已知的能够裂解硫酸乙酰肝素的内切糖苷酶。Roneparstat和necuparanib是从肝素中获得的乙酰肝素酶抑制剂，目前正在人类中作为潜在的抗癌药物进行测试，其结构中含有乙二醇分裂的糖醛酸部分，可能是其强大的抑制活性。我们在这里描述了三糖GlcNS6S-GlcA-1,6anGlcNS（1）及其乙二醇拆分（gs）对应物GlcNS6S-gsGlcA-1,6anGlcNS（2）的总化学合成。不出所料，在乙酰肝素酶抑制试验中，化合物2的效力比1高一个数量级。使用分子建模技术，我们创建了1和2的3D模型，并已通过NOESY NMR实验验证。纯合成寡糖已使乙二醇拆分的葡萄糖醛酸的构象得以首次深入研究。以1的结构引入乙二醇拆分单元可增加构象柔韧性，并缩短两种氨基葡萄糖动机之间的距离，从而促进与乙酰肝素酶的相互作用。然而，通过比较2和ronparstat的相对活性，我们可以得出结论，乙
• Sugar Chips immobilized with synthetic sulfated disaccharides of heparin/heparan sulfate partial structure
  作者：Masahiro Wakao、Akihiro Saito、Koh Ohishi、Yuko Kishimoto、Tomoaki Nishimura、Michael Sobel、Yasuo Suda

  DOI：10.1016/j.bmcl.2008.01.069

  日期：2008.4

  carbohydrate-protein interactions. Herein, we report syntheses of novel sulfated oligosaccharides possessing heparin and heparan sulfate partial disaccharide structures, their immobilization on gold-coated chips to prepare array-type Sugar Chips, and evaluation of binding potencies of proteins by surface plasmon resonance (SPR) imaging technology. Sulfated oligosaccharides were efficiently synthesized from glucosamine

  碳水化合物芯片技术在碳水化合物-蛋白质相互作用的高通量评估方面具有巨大潜力。在此，我们报告了具有肝素和硫酸乙酰肝素部分二糖结构的新型硫酸化寡糖的合成，将它们固定在镀金芯片上以制备阵列型糖芯片，以及通过表面等离子体共振 (SPR) 成像技术评估蛋白质的结合效力。硫酸化寡糖由葡糖胺和糖醛酸部分有效合成。然后使用先前报道的方法将合成的硫酸化寡糖轻松固定在镀金芯片上。这种分析方法的有效性在芯片和肝素结合蛋白之间的结合实验中得到证实，
• Synthesis of heparin partial structures and their binding activities to platelets
  作者：Shuhei Koshida、Yasuo Suda、Michael Sobel、Julie Ormsby、Shoichi Kusumoto

  DOI：10.1016/s0960-894x(99)00550-8

  日期：1999.11

  A synthetic pentasaccharide corresponding to the antithrombin III-binding region in heparin was also found to bind to human platelets. To identify the platelet-binding site in the pentasaccharide which is expected to be a novel sequence in heparin responsible for its platelet-binding, five partial structures of this particular pentasaccharide were synthesized. In a competitive assay using [H-3]-heparin, a trisaccharide, O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-alpha-D-glucopyranosyl)-(1-->4)-O-(2-O-sulfo-alpha-L-idopyranosyluronic acid)-(1-->4)-2-deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranose, was concluded to be a high-affinity site for heparin's binding to platelets. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of oligomeric assemblies of a platelet-binding key disaccharide in heparin and their biological activities
  作者：Shuhei Koshida、Yasuo Suda、Michael Sobel、Shoichi Kusumoto

  DOI：10.1016/s0040-4039(00)01826-8

  日期：2001.2

  Heparin, highly sulfated glycosaminoglycan, binds to platelets. A key disaccharide unit in heparin was previously found to be responsible for the binding, and the Frequency of the disaccharide unit was important for the binding potency. A newly developed method based on the reductive amination was effectively applied to prepare structurally defined oligomeric assemblies possessing multiple units of the key disaccharide. From their platelet-binding activities measured by the competitive binding assay, the enhancement of the activity was clearly observed with increasing number of the key disaccharide. (C) 2001 Elsevier Science Ltd. All rights reserved.