2,3,4,6-terta-O-acetyl-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl isothiouronium bromide | 68636-39-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-terta-O-acetyl-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl isothiouronium bromide
• 英文别名: S-[O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranosyl]-isothiourea; hydrobromide；S-[O²,O³,O⁶-Triacetyl-O⁴-(tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranosyl]-isothioharnstoff; Hydrobromid；S-(Hepta-O-acetyl-β-cellobiosyl)-isothiuronium-bromid
• CAS: 68636-39-5
• 化学式: BrH*C₂₇H₃₈N₂O₁₇S
• 分子量: 775.58
• InChiKey: NYPROWXURWCXMR-MSLAPOLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.19
• 重原子数：
  48.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  261.66
• 氢给体数：
  2.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-terta-O-acetyl-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 在 sodium metabisulfite 、 水 作用下， 以 二氯甲烷 为溶剂， 生成 hepta-O-acetyl-1-thio-β-cellobiose
  参考文献：
  名称：

  电化学介导的 1-硫糖与呫吨衍生物的 S-糖基化

  摘要：

  描述了室温下苄基 C-H 键与 1-硫糖的有效电化学脱氢交叉偶联。直接 S-糖基化方案避免使用任何氧化剂，可以轻松获得各种糖基化呫吨衍生物，收率高达 91%。目前的电氧化反应具有原子经济性高、效率高、反应条件温和、环境友好、官能团耐受性好等特点。此外，初步的机理研究表明该反应涉及自由基过程。

  DOI：

  10.1021/acs.orglett.3c01185
• 作为产物：
  描述：

  硫脲 、 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 以 丙酮 为溶剂， 反应 0.05h， 以86%的产率得到2,3,4,6-terta-O-acetyl-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl isothiouronium bromide
  参考文献：
  名称：

  Synthesis of Interglycosidically S‐Linked 1‐Thio‐Oligosaccharides Under Microwave Irradiation

  摘要：

  Microwave irradiation (MWI) has accelerated the synthesis of S-(2,3,4,6-tetra- O-acetyl-beta-D-glucopyranosyl)thiouronium bromide (2a), whose reaction with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide (1a) in the presence of Et3N afforded stereoselectively the acetylated beta,beta-1-thiotrehalose 4a. Similarly, the respective D-galactopyranosyl 4b and 2-acetylamino-2-deoxy-D-glucopyranosyl 4c analog as well as 4,4'-di-O-(2,3,4,6-tetra-O-acetyl-beta-D- galactopyranosyl) 4d and 4,4'-di-O-(2,3,4,6-tetra-O-acetyl-alpha-D- glucopyranosyl) 4e derivatives of 2,2',3,3',6,6'-hexa-O-acetyl beta,beta-1- thiotrehalose were prepared.

  DOI：

  10.1080/07328300500282540

文献信息

• Design and Synthesis of Hydrolytically Stable Multivalent Ligands Bearing Thiodigalactoside Analogues for Peanut Lectin and Human Galectin-3 Binding
  作者：Alejandro J. Cagnoni、José Kovensky、María Laura Uhrig

  DOI：10.1021/jo500883v

  日期：2014.7.18

  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.
• A Study of Some S-(Polyacetyl-β-D-glycopyranosyl)-thiuronium Halides
  作者：William A. Bonner、James E. Kahn

  DOI：10.1021/ja01149a092

  日期：1951.5