1,6-anhydro-2-O-benzyl-4-O-(tetrahydropyran-2-yl)-β-D-glucopyranose | 215094-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,6-anhydro-2-O-benzyl-4-O-(tetrahydropyran-2-yl)-β-D-glucopyranose
• CAS: 215094-09-0
• 化学式: C₁₈H₂₄O₆
• 分子量: 336.385
• InChiKey: XZNTYGLORVGQFA-IMVOZMHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-2-O-benzyl-4-O-(tetrahydropyran-2-yl)-β-D-glucopyranose 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 乙酸肼 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and biological activity of a new anti-factor Xa pentasaccharide with a C-interglycosidic bond

  摘要：

  A mixed synthetic C, O-pentasaccharide 17 has been synthesized and shown to display an anti-factor Xa activity similar to that of the corresponding O-pentasaccharide 18. 17 represents the first example of a synthetic C-oligosaccharidic mimetic eliciting a significant biological response. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00252-7
• 作为产物：
  描述：

  1,6:2,3-dianhydro-4-O-(tetrahydropyran-2-yl)-β-D-mannopyranose 、 苯甲醇钠 以 苯甲醇 为溶剂， 以95%的产率得到1,6-anhydro-2-O-benzyl-4-O-(tetrahydropyran-2-yl)-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis and biological activity of a new anti-factor Xa pentasaccharide with a C-interglycosidic bond

  摘要：

  A mixed synthetic C, O-pentasaccharide 17 has been synthesized and shown to display an anti-factor Xa activity similar to that of the corresponding O-pentasaccharide 18. 17 represents the first example of a synthetic C-oligosaccharidic mimetic eliciting a significant biological response. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00252-7

文献信息

• Introducing a C -interglycosidic bond in a biologically active pentasaccharide hardly affects its biological properties
  作者：Maurice Petitou、Jean-Pascal Hérault、Jean-Claude Lormeau、Arnim Helmboldt、Jean-Maurice Mallet、Pierre Sinaÿ、Jean-Marc Herbert

  DOI：10.1016/s0968-0896(98)00094-7

  日期：1998.9

  We describe here the synthesis and the biological activity of a 'C-pentasaccharide', a new analogue of the antithrombin III (AT III) binding region of heparin containing a methylene bridge in place of an interglycosidic oxygen atom. The affinity for AT III and the anti-factor Xa activity of this compound have been compared with that of the corresponding selected 'O-pentasaccharide'. Such a structural modification slightly decreased the affinity of this compound for AT III as well as its anti-factor Xa activity (880 +/- 40 anti-Xa units versus 1180 +/- 30 anti-Xa units for the C-pentasaccharide and the O-pentasaccharide, respectively). This compound therefore represents the first example of a new class of anti-factor Xa pentasaccharides containing a C-interglycosidic bond. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.