methyl(benzyl 2,3-di-O-methyl-β-D-glucopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside | 219595-98-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl(benzyl 2,3-di-O-methyl-β-D-glucopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: benzyl (2S,3S,4S,5R,6R)-3-hydroxy-4,5-dimethoxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxyoxane-2-carboxylate
• CAS: 219595-98-9
• 化学式: C₄₃H₅₀O₁₂
• 分子量: 758.863
• InChiKey: IVEHTRQKIGNRJD-JWPXJQIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  55
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  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)-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， 以69%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)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Identification of a hexasaccharide sequence able to inhibit thrombin and suitable for ‘polymerisation’

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(99)00067-1
• 作为产物：
  描述：

  benzyl (4-O-levulinyl-2,3-di-O-methyl-1-O-trichloroacetimidoyl-D-glucopyranos)uronate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 一水合肼 、 溶剂黄146 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 methyl(benzyl 2,3-di-O-methyl-β-D-glucopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Identification of a hexasaccharide sequence able to inhibit thrombin and suitable for ‘polymerisation’

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(99)00067-1

文献信息

• First Synthetic Carbohydrates with the Full Anticoagulant Properties of Heparin
  作者：Maurice Petitou、Philippe Duchaussoy、Pierre-A. Driguez、Guy Jaurand、Jean-P. Hérault、Jean-C. Lormeau、Constant A. A. van Boeckel、Jean-M. Herbert

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

  日期：1998.11.16

  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.