2,5-anhydro-3,4-di-O-benzoyl-D-mannitol | 121635-46-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-3,4-di-O-benzoyl-D-mannitol
• 英文别名: 2,5-Anhydro-3,4-di-O-benzoyl-D-mannitol；[(2R,3R,4R,5R)-4-benzoyloxy-2,5-bis(hydroxymethyl)oxolan-3-yl] benzoate
• CAS: 121635-46-9
• 化学式: C₂₀H₂₀O₇
• 分子量: 372.375
• InChiKey: USXNZXPYTRHNQW-BRSBDYLESA-N

物化性质

• 熔点：
  120-122 °C(Solv: toluene (108-88-3))
• 沸点：
  553.2±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-3,4-di-O-benzoyl-D-mannitol 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 2,5-anhydro-1-O-β-maltopyranosyl-D-mannitol
  参考文献：
  名称：

  Synthesis of poly-O-sulfated glycosides of 2,5-anhydro-d-mannitol

  摘要：

  2,5-Anhydro-3-O-beta-D-glucopyranosyl-; -3-O-alpha-D-idopyranosyl-; -3-O-alpha-D-arabinopyranosyl-; -3-O-alpha-L-arabinopyranosyl--; -3-0-beta-D-maltopyranosyl-; -3-O-beta-D-gentiobiopyranosyl-; -1,6-di-O-beta-D-glucopyranosyl-; -1,6-di-O-alpha-L-idopyranosyl,-; -1-O-beta-D-maltopyranosyl-.- -1,3,.6-tri-O-beta-D-glucopyranosyl-; -1,6-di-O-beta-maltopyranosyl- and -1,6-di-O-beta-D-gentiobiopyranosyl-2,5-anhydro-D-mannitol as well as their poly-O-sulfated derivatives were synthesized. The IP3-IC50 values of their sodium and/or potassium salts were determined for structure-activity studies aiming at the synthesis of new, orally active antiasthmatic compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.05.006
• 作为产物：
  描述：

  (2R,3R,4R,5R)-3,4-dihydroxy-2,5-di(trityloxymethyl)tetrahydrofuran 在 吡啶 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 4.0h， 生成 2,5-anhydro-3,4-di-O-benzoyl-D-mannitol
  参考文献：
  名称：

  Synthesis of poly-O-sulfated glycosides of 2,5-anhydro-d-mannitol

  摘要：

  2,5-Anhydro-3-O-beta-D-glucopyranosyl-; -3-O-alpha-D-idopyranosyl-; -3-O-alpha-D-arabinopyranosyl-; -3-O-alpha-L-arabinopyranosyl--; -3-0-beta-D-maltopyranosyl-; -3-O-beta-D-gentiobiopyranosyl-; -1,6-di-O-beta-D-glucopyranosyl-; -1,6-di-O-alpha-L-idopyranosyl,-; -1-O-beta-D-maltopyranosyl-.- -1,3,.6-tri-O-beta-D-glucopyranosyl-; -1,6-di-O-beta-maltopyranosyl- and -1,6-di-O-beta-D-gentiobiopyranosyl-2,5-anhydro-D-mannitol as well as their poly-O-sulfated derivatives were synthesized. The IP3-IC50 values of their sodium and/or potassium salts were determined for structure-activity studies aiming at the synthesis of new, orally active antiasthmatic compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.05.006

文献信息

• Glycosides and Salts Thereof
  申请人：Kuszmann Janos

  公开号：US20080249165A1

  公开（公告）日：2008-10-09

  The invention relates to new polysulfated glycosides of formula (I), the salts thereof formed with alkali metals or alkaline-earth metals, as well as the pharmaceutical compositions containing these compounds as active ingredients. Furthermore the invention provides a method of preventing, treating or alleviating the symptoms of acute and chronic inflammatory disorders of the airways of mammals—including asthma and asthma-related pathologies.

  该发明涉及公式（I）的新多硫酸基糖苷，以及与碱金属或碱土金属形成的盐，以及含有这些化合物作为活性成分的药物组合物。此外，该发明提供了一种预防、治疗或缓解哺乳动物呼吸道急性和慢性炎症性疾病症状的方法，包括哮喘和与哮喘相关的病理学。
• Glycodynamers: Dynamic Polymers Bearing Oligosaccharides Residues − Generation, Structure, Physicochemical, Component Exchange, and Lectin Binding Properties
  作者：Yves Ruff、Eric Buhler、Sauveur-Jean Candau、Ellina Kesselman、Yeshayahu Talmon、Jean-Marie Lehn

  DOI：10.1021/ja9082733

  日期：2010.3.3

  Dynamic glycopolymers have been generated by polycondensation through acylhydrazone formation between components bearing lateral bioactive oligosaccharide chains. They have been characterized as bottlebrush type by cryo-TEM and SANS studies. They present remarkable fluorescence properties whose emission wavelengths depend on the constitution of the polymer and are tunable by constitutional modification through exchange/incorporation of components, thus also demonstrating their dynamic character. Constitution-dependent binding of these glycodynamers to a lectin, peanut agglutinin, has been demonstrated.
• Synthesis of poly-O-sulfated glycosides of 2,5-anhydro-d-mannitol
  作者：János Kuszmann、Gábor Medgyes、Sándor Boros

  DOI：10.1016/j.carres.2005.05.006

  日期：2005.7

  2,5-Anhydro-3-O-beta-D-glucopyranosyl-; -3-O-alpha-D-idopyranosyl-; -3-O-alpha-D-arabinopyranosyl-; -3-O-alpha-L-arabinopyranosyl--; -3-0-beta-D-maltopyranosyl-; -3-O-beta-D-gentiobiopyranosyl-; -1,6-di-O-beta-D-glucopyranosyl-; -1,6-di-O-alpha-L-idopyranosyl,-; -1-O-beta-D-maltopyranosyl-.- -1,3,.6-tri-O-beta-D-glucopyranosyl-; -1,6-di-O-beta-maltopyranosyl- and -1,6-di-O-beta-D-gentiobiopyranosyl-2,5-anhydro-D-mannitol as well as their poly-O-sulfated derivatives were synthesized. The IP3-IC50 values of their sodium and/or potassium salts were determined for structure-activity studies aiming at the synthesis of new, orally active antiasthmatic compounds. (c) 2005 Elsevier Ltd. All rights reserved.