Ethyl 4,6-O-benzylidene-3-O-methyl-1-thio-β-D-glucopyranoside | 226064-78-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 4,6-O-benzylidene-3-O-methyl-1-thio-β-D-glucopyranoside
• 英文别名: (4aR,6S,7R,8R,8aR)-6-ethylsulfanyl-8-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 226064-78-4
• 化学式: C₁₆H₂₂O₅S
• 分子量: 326.414
• InChiKey: WFVNREYTTGWFFS-ULFACSLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 4,6-O-benzylidene-3-O-methyl-1-thio-β-D-glucopyranoside 在 三乙基硅烷 、 sodium hydride 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 Ethyl 2,6-di-O-benzyl-3-O-methyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  New synthetic heparin mimetics able to inhibit thrombin and factor Xa

  摘要：

  Synthetic pentadeca-, heptadeca- and nonadecasaccharides, comprising an antithrombin III (AT III) binding pentasaccharide prolonged at the non-reducing end by a thrombin binding domain have been obtained. The pentadecasaccharide is the shortest oligosaccharide able to catalyse thrombin inhibition by AT III. The nonadecasaccharide is a more potent thrombin inhibitor than standard heparin. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00155-9
• 作为产物：
  描述：

  3-O-methyl-D-glucopyranose 在 吡啶 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 19.5h， 生成 Ethyl 4,6-O-benzylidene-3-O-methyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  New synthetic heparin mimetics able to inhibit thrombin and factor Xa

  摘要：

  Synthetic pentadeca-, heptadeca- and nonadecasaccharides, comprising an antithrombin III (AT III) binding pentasaccharide prolonged at the non-reducing end by a thrombin binding domain have been obtained. The pentadecasaccharide is the shortest oligosaccharide able to catalyse thrombin inhibition by AT III. The nonadecasaccharide is a more potent thrombin inhibitor than standard heparin. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00155-9

文献信息

• Synthetic polysaccharides, preparation method therefor and pharmaceutical compositions containing same
  申请人：Sanofi-Synthelabo

  公开号：US06534481B1

  公开（公告）日：2003-03-18

  A synthetic polysaccharide including an antithrombin III binding domain consisting of a concatenation of five monosaccharides supporting a total of two carboxylic acid functions and at least four sulpho groups, said domain being directly bound at the non-reducing end by a thrombin binding domain including a concatenation of 10-25 monosaccharide units selected from hexoses, pentoses or deoxy sugars of which all the hydroxyl groups are etherified by a C1-6 alkyl group or esterified in the form of sulpho groups, as well as salts and particularly pharmaceutically acceptable salts thereof, are disclosed.

  一种合成多糖包括一个抗凝血酶III结合结构域，由五个单糖串联而成，支持总共两个羧基功能和至少四个磺酸基团，所述结构域直接与非还原端结合，包括一个由10-25个单糖单位串联而成的凝血酶结合结构域，所述单糖单位选自六糖、五糖或脱氧糖，其中所有羟基均由C1-6烷基基团醚化或以磺酸基团酯化，以及其盐和特别是药用可接受的盐。
• 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.
• POLYSACCHARIDES SYNTHETIQUES, PROCEDE POUR LEUR PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SANOFI-SYNTHELABO

  公开号：EP0912613B1

  公开（公告）日：2002-09-25
• US6534481B1
  申请人：——

  公开号：US6534481B1

  公开（公告）日：2003-03-18
• Experimental Proof for the Structure of a Thrombin-Inhibiting Heparin Molecule
  作者：Maurice Petitou、Anne Imberty、Philippe Duchaussoy、Pierre-Alexandre Driguez、Marie-Line Ceccato、Françoise Gourvenec、Philippe Sizun、Jean-Pascal Hérault、Serge Pérez、Jean-Marc Herbert

  DOI：10.1002/1521-3765(20010216)7:4<858::aid-chem858>3.0.co;2-n

  日期：2001.2.16

  Kinetic studies of thrombin inhibition by antithrombin in the presence of heparin have shown that thrombin binds to heparin in a preformed heparin - antithrombin complex. To study the relative position of the thrombin binding domain and the antithrombin binding domain on a heparin molecule we have designed and synthesized heparin mimetics which structurally are very similar to the genuine polysaccharide. Their inhibitory properties with respect to factor Xa and thrombin provide experimental evidence that in heparin the thrombin binding domain must be located at the nonreducing end of the antithrombin binding domain to observe thrombin inhibition. As expected, factor Xa inhibition is not affected by elongation of the antithrombin binding pentasaccharide sequence, regardless of the position in which this elongation takes place.