(2S,3S,4S,5R)-2-(methoxycarbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate) | 1185745-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R)-2-(methoxycarbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate)
• CAS: 1185745-10-1
• 化学式: C₂₄H₃₆Cl₃NO₁₀
• 分子量: 604.91
• InChiKey: FANHLISYPIYXDK-JYMWAKCPSA-N

物化性质

• 沸点：
  530.2±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  38.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  147.51
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R)-2-(methoxycarbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate) 、 (E)-4-[3-methoxy-5-(tert-butyldimethylsilyloxy)styryl]phenol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以60%的产率得到
  参考文献：
  名称：

  Neuroprotective and Anti-inflammatory Effects of Pterostilbene Metabolites in Human Neuroblastoma SH-SY5Y and RAW 264.7 Macrophage Cells

  摘要：

  Oxidative stress is known to be a key factor in many neurodegenerative diseases. Inflammation also plays a relevant role in a myriad of pathologies such as diabetes and atherosclerosis. Polyphenols coming from dietary sources, such as pterostilbene, may be beneficial in this type of diseases. However, most of them are rapidly metabolized and excreted, yielding very low phenolic bioavailability what makes it difficult to find out which are the mechanisms responsible for the observed bioactivity. Herein, we evaluate the effects of pterostilbene and its metabolites against H2O2-induced cell damage in human neuroblastoma SH-SY5Y cells and against lipopolysaccharide (LPS)-challenged RAW 264.7 macrophages. Among the metabolites tested, 3-methyl-4'-glucuronate-resveratrol (also called 4'-glucuronate pinostilbene, PIN-GlcAc, 11) prevented neuronal death via attenuation of reactive oxygen species (ROS) levels and increased RED OX activity in neurons. This compound is also able to ameliorate LPS-mediated inflammation on macrophages via inhibition of IL-6 and NO production. Thus, polyphenol from dietary sources could be part of potential functional foods designed to ameliorate the onset and progression of certain neurodegenerative diseases via oxidative stress reduction.

  DOI：

  10.1021/acs.jafc.9b07147

文献信息

• Glycodendrimers as Chondroitin Sulfate Mimetics: Synthesis and Binding to Growth Factor Midkine
  作者：Pedro Domínguez-Rodríguez、José J. Reina、Sergio Gil-Caballero、Pedro M. Nieto、José L. de Paz、Javier Rojo

  DOI：10.1002/chem.201701890

  日期：2017.8.22

  Chondroitin sulfate (CS) is a member of the glycosaminoglycan (GAG) family, a class of polysaccharides implicated in relevant biological functions. The structural complexity of these carbohydrates demands the development of simple glycomimetics as useful tools to study the biological processes in which GAGs are involved. In this work we described the synthesis of the disaccharide unit of the CS-E (GlcA-GalNAc(4

  硫酸软骨素（CS）是糖胺聚糖（GAG）家族的成员，该家族是一类涉及相关生物学功能的多糖。这些碳水化合物的结构复杂性要求开发简单的模拟糖类作为研究GAG参与的生物学过程的有用工具。在这项工作中，我们以多价形式描述了CS-E的二糖单元（GlcA-GalNAc（4,6-di-OSO 3））的合成。使用荧光偏振竞争测定法，我们已经证明了该二糖的六价树状大分子在低微摩尔范围内与中期因子相互作用。该结果突出显示了这些二糖展示多价系统作为更长和合成上更复杂的GAG寡糖的有趣模拟物的潜力。
• WO2020244483A5
  申请人：——

  公开号：WO2020244483A5

  公开（公告）日：2023-02-22
• A concise synthesis of glucuronide metabolites of urolithin-B, resveratrol, and hydroxytyrosol
  作者：Ricardo Lucas、David Alcantara、Juan Carlos Morales

  DOI：10.1016/j.carres.2009.05.016

  日期：2009.7

  A simple and direct strategy to chemically synthesize O-beta-D-glucuronides of urolithin-B 4, resveratrol 5, and the corresponding hydroxytyrosol derivatives 6, 7 (as a regioisomeric mixture), and 8 is described. The critical glycosylation step has been optimized using a structurally simple phenol, urolithin-B, by modification of several reaction parameters (solvent, promoter, and glucuronide donor). Very high yields have been obtained in the first synthesis of the O-beta-D-glucuronide of urolithin-B 4. Extension of these reaction conditions was used for the synthesis of resveratrol-3-O-glucuronide 5 where a higher yield than previously reported was obtained by using the much more common trichloroacetimidate glucuronide donor. Finally, three O-beta-D-glucuronides of hydroxytyrosol 6, 7, and 8 have been synthesized for the first time using chemical synthesis. (C) 2009 Elsevier Ltd. All rights reserved.