1,4-dimethoxy-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene | 210817-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-dimethoxy-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene
• 英文别名: (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dimethoxybenzene；[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-(2,5-dimethoxyphenyl)oxan-2-yl]methyl acetate
• CAS: 210817-42-8
• 化学式: C₂₂H₂₈O₁₁
• 分子量: 468.458
• InChiKey: UJGWNOLAZZTCSP-TWGBQZSLSA-N

物化性质

• 沸点：
  531.6±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,4-dimethoxy-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene 在 硝酸铵 、 N-溴代丁二酰亚胺(NBS) 、 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 5.0h， 生成 5-bromo-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-benzoquinone
  参考文献：
  名称：

  卤素取代的（C -β-d-吡喃葡萄糖基）-氢醌区域异构体：合成，酶学评价及其与糖原磷酸化酶的结合

  摘要：

  的电卤化Ç - （2,3,4,6-四- ø -乙酰基β- d吡喃葡萄糖基）-1,4-二甲氧基苯（1区域选择性地得到产品的卤化）对位位置到d -glucosyl部分（8，9）被脱乙酰化为3（氯化物）和16（溴化物）。为了制备间位异构体，用CAN有效地氧化1以提供C-（2,3,4,6-四-O-乙酰基-β- d-吡喃葡萄糖基）1,4-苯醌2，在MeOH或H中2 O-THF含有很少当量的AcCl，加入盐酸后主要生成间位（相对于糖部分而言）氯化氢醌衍生物5和18，后者被脱乙酰基化为4。脱乙酰化的元（4，5）或对位（3，16）halohydroquinones评价为通过动力学和X-射线晶体学糖原磷酸化酶（GP，对于在高葡萄糖浓度肝糖原分解的抑制的分子靶标）的抑制剂。这些化合物相对于α- d是GPb的竞争性抑制剂-葡萄糖-1-磷酸。所测量的IC 50值（μM）[169.9±10.0（3），95（4），39

  DOI：

  10.1016/j.bmc.2011.07.024
• 作为产物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 、 对苯二甲醚 在 silver trifluoromethanesulfonate 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以52%的产率得到1,4-dimethoxy-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene
  参考文献：
  名称：

  C-Glycosylated Aryl Tins: Versatile Building Blocks for ArylC-Glycoside Glycomimetics

  摘要：

  C-glycosylated aryl tins have been prepared as versatile building blocks of physiologically stable glycomimetics for glycoepitopes that have been recognized to serve biologically important roles in cell biochemistry.

  DOI：

  10.1080/07328309908544002

文献信息

• In the Search of Glycogen Phosphorylase Inhibitors: Synthesis of C-D-Glycopyranosylbenzo(hydro)quinones – Inhibition of and Binding to Glycogen Phosphorylase in the Crystal
  作者：Li He、Yun Zhi Zhang、Marcelle Tanoh、Guo-Rong Chen、Jean-Pierre Praly、Evangelia D. Chrysina、Costas Tiraidis、Magda Kosmopoulou、Demetres D. Leonidas、Nikos G. Oikonomakos

  DOI：10.1002/ejoc.200600548

  日期：2007.2

  23 were found to be competitive inhibitors of rabbit muscle glycogen phosphorylase b (GPb), with respect to the substrate α-D-glucose-1-phosphate, with Ki values of 1.3 and 0.9 mM, respectively, whereas C-β-D-glucosylhydroquinone 17 was not effective up to a concentration of 8 mM. In order to elucidate the structural basis of inhibition, we determined the crystal structures of 19 and 23 in complex

  五-O-乙酰基-β-D-吡喃葡萄糖和 1,4-二甲氧基苯通过亲电取代选择性引导为 C-β-D-吡喃葡萄糖基-1,4-二甲氧基苯，通过简单有效的反应（氧化、还原和脱乙酰化）转化为 C-β-D-吡喃葡萄糖基-1,4-二甲氧基苯) 到相应的 C-糖基氢-和 C-糖基苯醌，具有乙酰化或脱保护的糖部分。发现 C-β-D-葡萄糖基苯醌 19 和 C-β-D-葡萄糖基氢醌 23 是兔肌糖原磷酸化酶 b (GPb) 的竞争性抑制剂，相对于底物 α-D-葡萄糖-1-磷酸，Ki值分别为 1.3 和 0.9 mM，而 C-β-D-葡糖基氢醌 17 在浓度高达 8 mM 时无效。为了阐明抑制的结构基础，我们确定了 19 和 23 与 GPb 复合物在 2.03-2 的晶体结构。05 决议。复杂的结构表明抑制剂可以容纳在与 α-D-葡萄糖大致相同的位置的催化位点，并通过与该环的 Asp283 和 Asn284 的几个有利接触来稳定
• C-Glycopyranosyl-1,4-benzoquinones and -hydroquinones opening access to C-glycosylated analogs of vitamin E
  作者：Jean-Pierre Praly、Li He、Bing Bing Qin、Marcelle Tanoh、Guo-Rong Chen

  DOI：10.1016/j.tetlet.2005.07.125

  日期：2005.10

  2-(Per-O-acetyl-beta-D-glycopyranosyl)-1,4-dimethoxybenzenes led to C-glycosyl-hydroquinones suitable for preparing C-glycosylated analogs of vitamin E, having the sugar moiety free or acetylated. (c) 2005 Elsevier Ltd. All rights reserved.
• <i>C</i>-Glycosyl Amino-Substituted Hydro- and Benzoquinones: Synthesis and Preliminary Biological Evaluation
  作者：Jean-Pierre Praly、Yun Zhang、Kaïss Aouadi、Guo-Rong Chen

  DOI：10.1055/s-2007-990856

  日期：2007.11

  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.
• Synthesis of triazole-linked β-C-glycosyl dimers as inhibitors of PTP1B
  作者：Li Lin、Qiang Shen、Guo-Rong Chen、Juan Xie

  DOI：10.1016/j.bmc.2008.09.066

  日期：2008.11

  Protein tyrosine phosphatase 1B (PTP1B) has emerged as a promising target for type 2 diabetes. We have successfully synthesized dimeric acetylated and benzoylated beta-C-D-glucosyl and beta-C-D-galactosyl 1,4-dimethoxy benzenes or naphthalenes by click chemistry. These compounds were further transformed into the corresponding beta-C-D-glycosyl-1,4-quinone derivatives by CAN oxidation. The in vitro inhibition test showed that dimeric benzoylated beta-C-D-glycosyl 1,4-dimethoxybenzenes or 1,4-benzoquinones were good inhibitors of PTP1B (IC50: 0.62-0.88 mu M), with no significant difference between gluco and galacto derivatives. (C) 2008 Elsevier Ltd. All rights reserved.
• β-C-Glycosiduronic acids and β-C-glycosyl compounds: New PTP1B inhibitors
  作者：Li Lin、Qiang Shen、Guo-Rong Chen、Juan Xie

  DOI：10.1016/j.bmcl.2008.10.091

  日期：2008.12

  beta-C-Glycosiduronic acid quinones and beta-C-glycosyl compounds have been synthesized as sugar-based PTP1B inhibitors. Benzoyl protected quinone derivatives (14 and 35) as well as aryl beta-C-glycosyl compounds (18, 22, 23 and 34) showed IC50 values of 0.77-5.27 mu M against PTP1B, with compounds 18 and 23 bearing an acidic function being the most potent. (C) 2008 Elsevier Ltd. All rights reserved.