6-Desoxy-6-acetylmercapto-2,3,4-tri-O-acetyl-α-D-glucopyranosylbromid | 97169-77-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-Desoxy-6-acetylmercapto-2,3,4-tri-O-acetyl-α-D-glucopyranosylbromid
• 英文别名: 2,3,4-Tri-O-acetyl-6-S-acetyl-6-thio-α-D-glucopyranosylbromid；[(2S,3S,4S,5R,6R)-4,5-diacetyloxy-2-(acetylsulfanylmethyl)-6-bromooxan-3-yl] acetate
• CAS: 97169-77-2
• 化学式: C₁₄H₁₉BrO₈S
• 分子量: 427.27
• InChiKey: ISRSRGXHHPKRIP-RGDJUOJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  6-Desoxy-6-acetylmercapto-2,3,4-tri-O-acetyl-α-D-glucopyranosylbromid 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 25.5h， 生成
  参考文献：
  名称：

  Design and Synthesis of Hydrolytically Stable Multivalent Ligands Bearing Thiodigalactoside Analogues for Peanut Lectin and Human Galectin-3 Binding

  摘要：

  Herein, we describe the design and synthesis of a novel family of hydrolytically stable glycoclusters bearing thiodigalactoside (TDG) analogues as recognition elements of beta-galactoside binding lectins. The TDG analogue was synthesized by thioglycosylation of a 6-S-acetyl-alpha-D-glucosyl bromide with the isothiouronium salt of 2,3,4,6-tetra-O-acetyl-beta-D-galactose. Further propargylation of the TDG analogue allowed the coupling to azido-functionalized oligosaccharide scaffolds through copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) under microwave activation. The final mono-, di-, and tetravalent ligands were resistant to enzymatic hydrolisis by Escherichia coli beta-galactosidase. Binding affinities to peanut agglutinin and human galectin-3 were measured by isothermal titration calorimetry which showed K-a constants in the micromolar range as well as a multivalent effect. Monovalent ligand exhibited a binding affinity higher than that of thiodigalactoside. Docking studies performed with a model ligand on both beta-galactoside binding lectins showed additional interactions between the triazole ring and lectin amino acid residues, suggesting a positive effect of this aromatic residue on the biological activity.

  DOI：

  10.1021/jo500883v
• 作为产物：
  描述：

  D-葡萄糖 在 溴化钛(IV) 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 6-Desoxy-6-acetylmercapto-2,3,4-tri-O-acetyl-α-D-glucopyranosylbromid
  参考文献：
  名称：

  一种Sulfavant的合成方法

  摘要：

  本发明公开了一种Sulfavant的合成方法，属于有机合成技术领域。本发明中的Sulfavant合成方法基于新设计的合成路线，可以有效改善以往合成路线冗长、复杂的特性，整个过程的反应条件温和，后处理简单，所需药品廉价易得，中间产物采用一锅法进行合成，省去了后续实验处理及分离纯化的操作时间，使整个反应过程时间大幅缩短。

  公开号：

  CN117164649A

文献信息

• A New Approach to Some 1,6-Dideoxy 1,6-Epithio Sugars
  作者：H Driguez、JC Mcauliffe、RV Stick、DMG Tilbrook、SJ Williams

  DOI：10.1071/ch9960343

  日期：——

  The treatment of hexopyranosyl bromides, also activated at C6 (Br, OTs, OMs), with H2S/HCONMe2 under basic conditions gives rise to 1,6-dideoxy 1,6-epithio sugars. One such sugar has been further transformed into the synthetically useful 3,4-anhydro-1,6-dideoxy-1,6-epithio-β-D-galactose. The treatment of this epoxide with sodium azide and with cyclohexylamine is described. An analogous treatment of one doubly activated hexopyranosyl bromide with sodium hydrogen selenide has led to a novel 1,6-dideoxy 1,6-episeleno sugar which displayed interesting n.m.r. spectra. Finally, in an attempt to prepare 1,6-dideoxy 1,6-epidithio sugars, a tetraalkylammonium tetrathiomolybdate reagent was found to be the reagent of choice for converting doubly activated hexopyranosyl bromides into 1,6-dideoxy 1,6-epithio sugars.

  在碱性条件下，用 H2S/HCONMe2 处理同样在 C6 处活化的溴化六吡喃糖（Br、OTs、OMs），会产生 1,6-二脱氧 1,6-epithio 糖。其中一种糖被进一步转化为对合成有用的 3,4-脱氢-1,6-二脱氧-1,6-环硫代-β-D-半乳糖。文中介绍了用叠氮化钠和环己胺处理这种环氧化物的方法。用硒化氢钠对一种双活化的溴化六吡喃糖进行类似处理后，得到了一种新型的 1,6-二脱氧 1,6-episeleno 糖，它显示出有趣的 n.m.r. 光谱。最后，在尝试制备 1,6-二脱氧 1,6-epidithio 糖时，发现四烷基钼酸四铵试剂是将双活化溴化己吡喃糖基转化为 1,6-二脱氧 1,6-epithio 糖的首选试剂。
• Facile and Versatile Chemoenzymatic Synthesis of Enterobactin Analogues and Applications in Bacterial Detection
  作者：Albert A. Lee、Yi-Chen S. Chen、Elisa Ekalestari、Sheng-Yang Ho、Nai-Shu Hsu、Tang-Feng Kuo、Tsung-Shing Andrew Wang

  DOI：10.1002/anie.201603921

  日期：2016.9.26

  by cognate transporters. Siderophore conjugates are thus a promising strategy for delivering functional reagents into bacteria. In this work, we present an easy‐to‐perform, one‐pot chemoenzymatic synthesis of functionalized monoglucosylated enterobactin (MGE). When functionalized MGE is conjugated to a rhodamine fluorophore, which affords RhB‐Glc‐Ent, it can selectively label Gram‐negative bacteria

  铁载体，如Enterobactin（Ent），是可以通过同源转运蛋白与铁一起选择性导入细菌的小分子。因此，铁载体缀合物是用于将功能性试剂递送到细菌中的有前途的策略。在这项工作中，我们提出了一种功能强大的单糖基化肠杆菌素（MGE）易于执行的一锅化学酶法合成方法。当将功能化的MGE与罗丹明荧光团缀合后可提供RhB-Glc-Ent，它可以选择性地标记利用Ent的革兰氏阴性细菌，包括一些大肠杆菌菌株和铜绿假单胞菌。霍乱弧菌利用线性化Ent的细菌，也可以被弱靶向。而且，该靶向在铁限制条件下有效，但在富铁条件下无效。我们的结果表明，RhB‐Glc‐Ent探针不仅对细菌菌株敏感，而且对环境中的铁状况也敏感。
• MILJKOVIC, DUSAN;VUKOJEVIC, NADA;MEDAKOVIC, DAMIR;BATTA, GYULA, CARBOHYDR. RES., 193,(1989) C. 275-278
  作者：MILJKOVIC, DUSAN、VUKOJEVIC, NADA、MEDAKOVIC, DAMIR、BATTA, GYULA

  DOI：——

  日期：——