Phenyl 4,6-O-benzylidene-2,3-di-O-methyl-1-thio-α-D-glucopyranoside | 226064-74-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phenyl 4,6-O-benzylidene-2,3-di-O-methyl-1-thio-α-D-glucopyranoside
• 英文别名: (4aR,6R,7R,8S,8aR)-7,8-dimethoxy-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 226064-74-0
• 化学式: C₂₁H₂₄O₅S
• 分子量: 388.485
• InChiKey: JKQSNRUQMPCBQH-BQUARMOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Phenyl 4,6-O-benzylidene-2,3-di-O-methyl-1-thio-α-D-glucopyranoside 在 三乙基硅烷 、 4 A molecular sieve 、 叔丁基二甲硅基三氟甲磺酸酯 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 0.17h， 生成 4-oxo-pentanoic acid 6-[5-acetoxy-2-benzyloxymethyl-6-(2-benzyloxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-methoxy-tetrahydro-pyran-3-yloxy]-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Experimental Proof for the Structure of a Thrombin-Inhibiting Heparin Molecule

  摘要：

  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.

  DOI：

  10.1002/1521-3765(20010216)7:4<858::aid-chem858>3.0.co;2-n
• 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 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 19.5h， 生成 Phenyl 4,6-O-benzylidene-2,3-di-O-methyl-1-thio-α-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

• 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
• 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.
• New synthetic heparin mimetics able to inhibit thrombin and factor Xa
  作者：Maurice Petitou、Philippe Duchaussoy、Pierre-A. Driguez、Jean-P. Hérault、Jean-C. Lormeau、Jean-M. Herbert

  DOI：10.1016/s0960-894x(99)00155-9

  日期：1999.4

  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.