2,5-anhydro-3-O-(α-D-arabinopyranosyl)-D-mannitol | 862607-69-0

• 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-O-(α-D-arabinopyranosyl)-D-mannitol
• 英文别名: (2R,3S,4R,5R)-2-[(2R,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4,5-triol
• CAS: 862607-69-0
• 化学式: C₁₁H₂₀O₉
• 分子量: 296.274
• InChiKey: DCKNMDCUYVLUFC-SJXPRXMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-3-O-(α-D-arabinopyranosyl)-D-mannitol 在 三氧化硫 、 potassium acetate 、 氢氧化钾 、 strontium(II) acetate 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 、 乙醇 、 水 为溶剂， 以90%的产率得到2,5-anhydro-1,4,6-tri-O-sulfato-3-O-(2,3,4-tri-O-sulfato-α-D-arabinopyranosyl)-D-mannitol hexa potassium salt
  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：

  三-O-乙酰基-β-D-溴化阿拉伯糖 在 sodium methylate 、 氰化汞 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 22.0h， 生成 2,5-anhydro-3-O-(α-D-arabinopyranosyl)-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

• [EN] GLYCOSIDES AND SALTS THEREOF<br/>[FR] GLYCOSIDES ET LEURS SELS
  申请人：IVAX CORP

  公开号：WO2006017727A2

  公开（公告）日：2006-02-16

  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.
• 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.