Ethyl 3-O-methyl-1-thio-β-D-glucopyranoside | 226069-82-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 3-O-methyl-1-thio-β-D-glucopyranoside
• CAS: 226069-82-5
• 化学式: C₉H₁₈O₅S
• 分子量: 238.305
• InChiKey: YQQMHOWFROERHN-HXLXBVJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.81
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.15
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Ethyl 3-O-methyl-1-thio-β-D-glucopyranoside 在 三乙基硅烷 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 乙酸肼 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 、 乙醚 、 乙醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 10.08h， 生成 Allyl 2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-β-D-glucopyranoside
  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：

  1,2:5,6-二异亚丙基-3-O-甲基-alpha-D-呋喃葡萄糖 在 甲醇 、 sodium methylate 作用下， 以 水 为溶剂， 反应 35.75h， 生成 Ethyl 3-O-methyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Oligosaccharides Self-Assemble and Show Intrinsic Optical Properties

  摘要：

  Self-assembling peptides and oligonucleotides have given rise to synthetic materials with several applications in nanotechnology. Aggregation of synthetic oligosaccharides into well-defined architectures has not been reported even though natural polysaccharides, such as cellulose and chitin, are key structural components of biomaterials. Here, we report that six synthetic oligosaccharides, ranging from dimers to hexamers, self-assemble into nanostructures of varying morphologies and emit within the visible spectrum in an excitation-dependent manner. Well-defined differences in chain length, monomer modification, and aggregation methods yield glycomaterials with distinct shapes and properties. The excitation-dependent fluorescence in a broad range within the visible spectrum illustrates their potential for use in optical devices and imaging applications. We anticipate that our systematic approach of studying well-defined synthetic oligosaccharides will form the foundation of our understanding of carbohydrate interactions in nature.

  DOI：

  10.1021/jacs.8b11882

文献信息

• 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.
• 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.