4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,5-dimethoxyaniline | 1004782-80-2

• 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: 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,5-dimethoxyaniline
• CAS: 1004782-80-2
• 化学式: C₂₂H₂₉NO₁₁
• 分子量: 483.472
• InChiKey: GRGRTFYSAARIQM-TWGBQZSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  158.91
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,5-dimethoxyaniline 在 甲醇 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 乙酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 N-(2,5-dimethoxy-4-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)-2-mercaptoacetamide
  参考文献：
  名称：

  Epimeric Monosaccharide−Quinone Hybrids on Gold Electrodes toward the Electrochemical Probing of Specific Carbohydrate−Protein Recognitions

  摘要：

  Carbohydrates represent one of the most significant natural building blocks, which govern numerous critical biological and pathological processes through specific carbohydrate-receptor interactions on the cell surface. We present here a new class of electrochemical probes based on gold surface-coated epimeric monosaccharide-quinone hybrids toward the ingenious detection of specific epimeric carbohydrate-protein interactions. Glucose and galactose, which represent a pair of natural monosaccharide C4 epimers, were used to closely and solidly conjugate with the 1,4-dimethoxybenzene moiety via a single C-C glycosidic bond, followed by the introduction of a sulfhydryl anchor. The functionalized aryl C-glycosides were sequentially coated on the gold electrode via the self-assembled monolayer (SAM) technique. X-ray photoelectron spectroscopy (XPS) was used to confirm the SAM formation, by which different binding energies (BE) between the glucosyl and the galactosyl SAMs on the surface, probably rendered by their epimeric identity, were observed. The subsequent electrochemical deprotection process readily furnished the surface-confined quinone/hydroquinone redox couple, leading to the formation of electrochemically active epimeric monosaccharide-quinone SAMs on the gold electrode. Cyclic voltammetry (CV) and differential pulse voltammetry (DPV) used for the detection of specific sugar-lectin interactions indicated that the addition of specific lectin to the corresponding monosaccharide-quinone surface, i.e., concanavalin A (Con A) to the glucosyl SAM and peanut agglutinin (PNA) to the galactosyl SAM, resulted in an obvious decrease in peak current, whereas the addition of nonspecific lectins to the same SAMs gave very minor current variations. Such data suggested our uniquely constructed gold surface coated by sugar-quinone hybrids to be applicable as electrochemical probes for the detection of specific sugar-protein interactions, presumably leading to a new electrochemistry platform toward the study of carbohydrate-mediated intercellular recognitions.

  DOI：

  10.1021/ja110478j
• 作为产物：
  描述：

  2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dimethoxy-5-nitrobenzene 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 1.25h， 以82%的产率得到4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,5-dimethoxyaniline
  参考文献：
  名称：

  C-Glycosyl Amino-Substituted Hydro- and Benzoquinones: Synthesis and Preliminary Biological Evaluation

  摘要：

  Reaction of C-beta-D-glycopyranosyl-1,4-dimethoxybenzenes with acetyl nitrate afforded 2-(beta-D-glycopyranosyl)-1,4-dimethoxy-5-nitrobenzenes in high yields. These were converted smoothly (reduction to amines, N-acylation, oxidation, and reduction) into the corresponding C-glycosyl-hydro(benzo)quinone derivatives, with different amide-based substituents at C-5. Reduction of the nitro compounds to amines proceeded smoothly by catalytic hydrogen transfer with HCO2NH4.

  DOI：

  10.1055/s-2007-990856