4-hydroxyphenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxyphenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
• 英文别名: 4-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyphenol
• 化学式: C₄₀H₄₀O₇
• 分子量: 632.753
• InChiKey: SWGRZGXCPLZRSF-JSMBFNCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-hydroxyphenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 、 苯甲醇 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 乙腈 为溶剂， 以60.784%的产率得到
  参考文献：
  名称：

  通过氧化活化对甲氧基苯基 (PMP) 糖苷进行化学糖基化

  摘要：

  开发了一种新型过硫酸盐介导的氧化糖基化系统，该系统使用对甲氧基苯基 (PMP) 糖苷作为稳定的糖基供体。该研究表明，作为氧化剂的K 2 S 2 O 8和作为路易斯酸催化剂的Hf(OTf) 4在将 PMP 基团氧化活化为潜在离去基团的过程中起着重要作用。这种方便的糖基化方案在温和条件下进行，并提供范围广泛的具有生物学和合成价值的糖缀合物，包括糖基氟化物。

  DOI：

  10.1021/acs.orglett.3c01050
• 作为产物：
  描述：

  对苯二酚 、 2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate 在 molecular sieve 、 三氟化硼-二甲醚络合物 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以69%的产率得到4-hydroxyphenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  从对苯二酚糖苷开始氧化诱导糖基化

  摘要：

  作为一类新的糖基供体，对苯二酚糖苷可用于糖基化反应。它们的活化可以电化学或在均相化学条件下进行。常规地，使用CH 2 Cl 2中的DDQ作为氧化剂，生产几种葡糖苷，产率大于77％。对于电解，优选使用三甲基氢醌的糖苷，因为它们的低氧化电位允许利用未分裂的细胞。糖基供体的合成通过使用三氟化硼醚化物作为催化剂，通过使酚与过乙酰化的单糖直接偶联而高效地实现。对苯二酚衍生物的氧化也可用于生成其他稳定的阳离子。

  DOI：

  10.1016/j.tet.2008.03.056

文献信息

• [EN] REAGENTS AND METHODS FOR GLYCOSYLATION<br/>[FR] RÉACTIFS ET MÉTHODES DE GLYCOSYLATION
  申请人：UNIV FLORIDA

  公开号：WO2018035416A1

  公开（公告）日：2018-02-22

  The invention provides methods and regents for the glycosylation of organic molecules. In one aspect, the invention provides a method for glycosylating a hydroxyl-containing organic compound (i.e., a glycosyl acceptor) comprising contacting a glycosyl donor with the hydroxyl-containing organic compound, in the presence of an oxidant, to yield a glycosylated organic compound. In certain embodiments, the methods provided herein provide glycosylation products with high anomeric selectivity. The methods can be applied to the synthesis of disaccharides, trisaccharides, polysaccharides, glycans, etc. Also provided herein are compounds (e.g., glycosyl donors and acceptors) which are useful building blocks in the provided reactions.

  这项发明提供了一种用于有机分子的糖基化的方法和试剂。在一个方面，该发明提供了一种用于糖基化含有羟基的有机化合物（即糖基受体）的方法，包括将糖基供体与含有羟基的有机化合物在氧化剂存在下接触，以产生糖基化的有机化合物。在某些实施例中，本文提供的方法提供了高各向异性选择性的糖基化产物。这些方法可以应用于二糖、三糖、多糖、糖类等的合成。本文还提供了在所述反应中有用的化合物（例如，糖基供体和受体），这些化合物是提供的反应中的构建模块。
• Stereoselective <i>O</i> ‐Glycosylations by Pyrylium Salt Organocatalysis**
  作者：Michael Martin Nielsen、Thomas Holmstrøm、Christian Marcus Pedersen

  DOI：10.1002/anie.202115394

  日期：2022.2

  A glycosylation method for non-specialists: Commercially available pyrylium salts catalyze stereoselective glycosylation reactions with trichloroacetimidate electrophiles. A wide range of phenolic nucleophiles are compatible with the procedure. The standard conditions involve mixing three components at ambient conditions and proceed with minimal formation of undesired by-products.

  非专业人士的糖基化方法：市售的吡喃盐催化立体选择性糖基化反应与三氯乙酰亚胺酯亲电子试剂。多种酚类亲核试剂与该程序兼容。标准条件包括在环境条件下混合三种组分，并以最少的不希望的副产物形成进行。
• A new synthesis of α-arbutin via Lewis acid catalyzed selective glycosylation of tetra-O-benzyl-α-d-glucopyranosyl trichloroacetimidate with hydroquinone
  作者：Zhao-Xia Wang、Xiao-Xin Shi、Guo-Rong Chen、Zhi-Hua Ren、Lei Luo、Jing Yan

  DOI：10.1016/j.carres.2006.04.022

  日期：2006.8

  α-Arbutin has huge application potentials in the cosmetic industry, as its inhibitory effect on human tyrosinase is stronger than that of its naturally occurring anomer arbutin (4-hydroxyphenyl β- d -glucopyranoside). Enzymatic synthesis was preferred for α-arbutin previously, and now a new chemical synthesis is reported. The reaction of tetra- O -benzyl-α- d -glucopyranosyl trichloroacetimidate, as glycosyl

  摘要α-熊果苷在化妆品工业中具有巨大的应用潜力，因为它对人酪氨酸酶的抑制作用强于其天然存在的端基熊果苷（4-羟苯基β-d-吡喃葡萄糖苷）。以前，酶促合成首选用于α-熊果苷，现在报道了一种新的化学合成方法。通过催化量的三甲基甲硅烷基三氟甲磺酸盐（TMSOTf）引发作为糖基供体的四-O-苄基-α-d-吡喃葡萄糖基三氯乙酰亚氨酸酯与对苯二酚的反应，生成4-羟基苯基2,3,4,6-四-O -苄基-α-d-吡喃葡萄糖苷具有高的立体选择性和产率，然后在脱保护后定量生成α-熊果苷。
• Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer’s Disease
  作者：Ana M. de Matos、M. Teresa Blázquez-Sánchez、Andreia Bento-Oliveira、Rodrigo F. M. de Almeida、Rafael Nunes、Pedro E. M. Lopes、Miguel Machuqueiro、Joana S. Cristóvão、Cláudio M. Gomes、Cleide S. Souza、Imane G. El Idrissi、Nicola A. Colabufo、Ana Diniz、Filipa Marcelo、M. Conceição Oliveira、Óscar López、José G. Fernandez-Bolaños、Philipp Dätwyler、Beat Ernst、Ke Ning、Claire Garwood、Beining Chen、Amélia P. Rauter

  DOI：10.1021/acs.jmedchem.0c00841

  日期：2020.10.22

  Despite the rapidly increasing number of patients suffering from type 2 diabetes, Alzheimer's disease, and diabetes-induced dementia, there are no disease-modifying therapies that are able to prevent or block disease progress. In this work, we investigate the potential of nature-inspired glucosylpolyphenols against relevant targets, including islet amyloid polypeptide, glucosidases, and cholinesterases. Moreover, with the premise of Fyn kinase as a paradigm-shifting target in Alzheimer's drug discovery, we explore glucosylpolyphenols as blockers of Aβ-induced Fyn kinase activation while looking into downstream effects leading to Tau hyperphosphorylation. Several compounds inhibit Aβ-induced Fyn kinase activation and decrease pTau levels at 10 μM concentration, particularly the per-O-methylated glucosylacetophloroglucinol and the 4-glucosylcatechol dibenzoate, the latter inhibiting also butyrylcholinesterase and β-glucosidase. Both compounds are nontoxic with ideal pharmacokinetic properties for further development. This work ultimately highlights the multitarget nature, fine structural tuning capacity, and valuable therapeutic significance of glucosylpolyphenols in the context of these metabolic and neurodegenerative disorders.
• Oxidatively induced glycosylation starting from hydroquinone glycosides
  作者：Hans Günter Thomas、Jean-Luc Mieusset

  DOI：10.1016/j.tet.2008.03.056

  日期：2008.5

  several glucosides were produced with yields greater than 77% using DDQ in CH2Cl2 as oxidizing agent. For electrolyses, glycosides of trimethylhydroquinone are preferably used because their low oxidation potentials allow the utilization of an undivided cell. The synthesis of the glycosyl donors was achieved with high efficiency by direct coupling of the phenols with peracetylated monosaccharides employing

  作为一类新的糖基供体，对苯二酚糖苷可用于糖基化反应。它们的活化可以电化学或在均相化学条件下进行。常规地，使用CH 2 Cl 2中的DDQ作为氧化剂，生产几种葡糖苷，产率大于77％。对于电解，优选使用三甲基氢醌的糖苷，因为它们的低氧化电位允许利用未分裂的细胞。糖基供体的合成通过使用三氟化硼醚化物作为催化剂，通过使酚与过乙酰化的单糖直接偶联而高效地实现。对苯二酚衍生物的氧化也可用于生成其他稳定的阳离子。