Toluene-4-sulfonic acid (1R,2S,3S,4R,5R)-3-hydroxy-2-(4-methoxy-phenoxy)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester | 203188-95-8

• 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: Toluene-4-sulfonic acid (1R,2S,3S,4R,5R)-3-hydroxy-2-(4-methoxy-phenoxy)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester
• 英文别名: 1,6-Anhydro-4-O-p-methoxyphenyl-2-O-tosyl-beta-D-glucopyranose；[(1R,2S,3S,4R,5R)-3-hydroxy-2-(4-methoxyphenoxy)-6,8-dioxabicyclo[3.2.1]octan-4-yl] 4-methylbenzenesulfonate
• CAS: 203188-95-8
• 化学式: C₂₀H₂₂O₈S
• 分子量: 422.456
• InChiKey: YSQZMEKWBNEWQX-USYVTKNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (1R,2S,3S,4R,5R)-3-hydroxy-2-(4-methoxy-phenoxy)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester 在 sodium hydride 、 苯甲醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (1R,2R,3S,4R,5R)-4-Benzyloxy-3-methoxy-2-(4-methoxy-phenoxy)-6,8-dioxa-bicyclo[3.2.1]octane
  参考文献：
  名称：

  Synthetic oligosaccharides having various functional domains: Potent and potentially safe heparin mimetics

  摘要：

  A synthetic heptadecasaccharide, comprising an antithrombin III binding domain, a thrombin binding domain, and a neutral methylated hexasaccharide sequence, was obtained through a convergent synthesis. This compound displayed in vitro anticoagulant properties similar to that of standard heparin but, in contrast with heparin, escaped neutralization by platelet factor 4, a protein released by activated platelets. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00156-0
• 作为产物：
  描述：

  1,6:3,4-二脱水-2-O-对甲苯磺酰基-beta-D-吡喃半乳糖 、 4-甲氧基苯酚 在 三氯化铝 作用下， 反应 0.33h， 以74%的产率得到Toluene-4-sulfonic acid (1R,2S,3S,4R,5R)-3-hydroxy-2-(4-methoxy-phenoxy)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester
  参考文献：
  名称：

  Synthetic oligosaccharides having various functional domains: Potent and potentially safe heparin mimetics

  摘要：

  A synthetic heptadecasaccharide, comprising an antithrombin III binding domain, a thrombin binding domain, and a neutral methylated hexasaccharide sequence, was obtained through a convergent synthesis. This compound displayed in vitro anticoagulant properties similar to that of standard heparin but, in contrast with heparin, escaped neutralization by platelet factor 4, a protein released by activated platelets. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00156-0

文献信息

• Synthetic polysaccharides, their method of production and pharmaceutical compositions containing same
  申请人：Sanofi-Synthelabo

  公开号：US06528497B1

  公开（公告）日：2003-03-04

  Novel synthetic polysaccharides for use in the treatment of pathologies associated with a coagulation dysfunction.

  用于治疗与凝血功能障碍相关的病理的新型合成多糖。
• Opening of levoglucosane derived epoxides with oxygen, nitrogen and sulfur nucleophiles
  作者：Wolfgang K.-D. Brill、Dominique Tirefort

  DOI：10.1016/s0040-4039(97)10715-8

  日期：1998.2

  A variety of nucleophiles were employed to open levoglucosane derived epoxides. (C) 1998 Elsevier Science Ltd. All rights reserved.
• POLYSACCHARIDES DE SYNTHESE, PROCEDE POUR LEUR PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LE CONTENANT
  申请人：SANOFI-SYNTHELABO

  公开号：EP1049721B1

  公开（公告）日：2001-11-21
• US6528497B1
  申请人：——

  公开号：US6528497B1

  公开（公告）日：2003-03-04
• Synthetic oligosaccharides having various functional domains: Potent and potentially safe heparin mimetics
  作者：Maurice Petitou、Pierre-Alexandre Driguez、Philippe Duchaussoy、Jean-Pascal Hérault、Jean-Claude Lormeau、Jean-Marc Herbert

  DOI：10.1016/s0960-894x(99)00156-0

  日期：1999.4

  A synthetic heptadecasaccharide, comprising an antithrombin III binding domain, a thrombin binding domain, and a neutral methylated hexasaccharide sequence, was obtained through a convergent synthesis. This compound displayed in vitro anticoagulant properties similar to that of standard heparin but, in contrast with heparin, escaped neutralization by platelet factor 4, a protein released by activated platelets. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.