methyl(benzyl 4-O-levulinyl-2,3-di-O-methyl-β-D-glucopyranosyluronate)-[(1->4)-(3,6-di-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-(1->4)-(benzyl 2,3-di-O-methyl-β-D-glucopyranosyluronate)]2-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside | 219596-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl(benzyl 4-O-levulinyl-2,3-di-O-methyl-β-D-glucopyranosyluronate)-[(1->4)-(3,6-di-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-(1->4)-(benzyl 2,3-di-O-methyl-β-D-glucopyranosyluronate)]2-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
• CAS: 219596-39-1
• 化学式: C₁₁₂H₁₃₂O₄₀
• 分子量: 2118.26
• InChiKey: DEPBOQAFYVZSQK-VNAZJJCMSA-N

反应信息

• 作为反应物：
  描述：

  methyl(benzyl 4-O-levulinyl-2,3-di-O-methyl-β-D-glucopyranosyluronate)-[(1->4)-(3,6-di-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-(1->4)-(benzyl 2,3-di-O-methyl-β-D-glucopyranosyluronate)]2-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  First Synthetic Carbohydrates with the Full Anticoagulant Properties of Heparin

  摘要：

  A single disaccharide building block is required to obtain synthetic carbohydrates that reproduce the anticoagulant activity of heparin and inhibit thrombin (n>6) and/or factor Xa (n≥2; see reaction scheme). Thus, there is evidence that heparin fragments with at least 15 saccharide units are required for thrombin inhibition. Lev=levulinoyl.

  DOI：

  10.1002/(sici)1521-3773(19981116)37:21<3009::aid-anie3009>3.0.co;2-f
• 作为产物：
  描述：

  Benzyl 4-O-levulinyl-2,3-di-O-methyl-β-D-glucopyranosyluronate-(1->4)-3,6-di-O-acetyl-2-O-benzyl-α/β-D-glucopyranosyl trichloroacetimidate 、 methyl(benzyl 2,3-di-O-methyl-β-D-glucopyranosyluronate)-(1->4)-(3,6-di-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-(1->4)-(benzyl 2,3-di-O-methyl-β-D-glucopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以63%的产率得到methyl(benzyl 4-O-levulinyl-2,3-di-O-methyl-β-D-glucopyranosyluronate)-[(1->4)-(3,6-di-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-(1->4)-(benzyl 2,3-di-O-methyl-β-D-glucopyranosyluronate)]2-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  First Synthetic Carbohydrates with the Full Anticoagulant Properties of Heparin

  摘要：

  A single disaccharide building block is required to obtain synthetic carbohydrates that reproduce the anticoagulant activity of heparin and inhibit thrombin (n>6) and/or factor Xa (n≥2; see reaction scheme). Thus, there is evidence that heparin fragments with at least 15 saccharide units are required for thrombin inhibition. Lev=levulinoyl.

  DOI：

  10.1002/(sici)1521-3773(19981116)37:21<3009::aid-anie3009>3.0.co;2-f

文献信息

• Identification of a hexasaccharide sequence able to inhibit thrombin and suitable for ‘polymerisation’
  作者：Philippe Duchaussoy、Guy Jaurand、Pierre-A. Driguez、Isidore Lederman、Françoise Gourvenec、Jean-M. Strassel、Philippe Sizun、Maurice Petitou、Jean-M. Herbert

  DOI：10.1016/s0008-6215(99)00067-1

  日期：1999.4

  Three hexasaccharides, having from low to very high affinity for antithrombin, were synthesised from disaccharide building block precursors. One of them, methyl(sodium 2,3-di-O-methyl-4-O-sodium sulfonato-alpha-L-idopyranosyluronate)-(1 --> 4)-[(2,3,6-tri-O-sodium sulfonato-alpha-D-glucopyranosyl)-(1 --> 4)-(sodium 2,3-di-O-methyl-alpha-L-idopyranosyluronate)-(1 --> 4)](2)-2,3,6-tri-O-sodium sulfonato-alpha-D-glucopyranoside, obtainable from a single disaccharide building block precursor, constitutes a good starting point for obtaining simple oligosaccharidic heparin mimetics able to inhibit the two coagulation factors thrombin and Factor Xa. (C) 1999 Elsevier Science Ltd. All rights reserved.