1,4-dimethoxy-2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)benzene | 189281-89-8

• 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-galactopyranosyl)benzene
• 英文别名: [(2R,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-(2,5-dimethoxyphenyl)oxan-2-yl]methyl acetate
• CAS: 189281-89-8
• 化学式: C₂₂H₂₈O₁₁
• 分子量: 468.458
• InChiKey: UJGWNOLAZZTCSP-FXTUREPZSA-N

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-galactopyranosyl)benzene 在 sodium tetrahydroborate 、 ammonium cerium(IV) nitrate 、 sodium sulfate 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 0.92h， 生成 2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)hydroquinone
  参考文献：
  名称：

  寻找糖原磷酸化酶抑制剂：CD-吡喃糖基苯并（氢）醌的合成——晶体中糖原磷酸化酶的抑制和结合

  摘要：

  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

  DOI：

  10.1002/ejoc.200600548
• 作为产物：
  描述：

  1,2,3,4,6-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82%的产率得到1,4-dimethoxy-2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)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

• : A powerful new promoter combination in the aryl C-glycosidation of a diverse range of sugar acetates and aromatic substrates
  作者：Takeshi Kuribayashi、Nobuyuki Ohkawa、Susumu Satoh

  DOI：10.1016/s0040-4039(98)00825-9

  日期：1998.6

  SnCl4/AgOTfa was shown to be a powerful combination for promoting aryl C-glycosidation between various sugar acetates and aromatic substrates. This promoter activates otherwise unreactive peracetylated glycosides, leaving them susceptible to reaction with low electron-donating aromatics. A survey of the reaction application is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
• The sequential double aryl C-glycosidation: Introduction of a second sugar unit onto mono aryl C-glycosides using
  作者：Takeshi Kuribayashi、Nobuyuki Ohkawa、Susumu Satoh

  DOI：10.1016/s0040-4039(98)00826-0

  日期：1998.6

  The promoter combination (SnCl4/AgOTfa) was successfully applied to introduce a second sugar unit onto mono aryl C-glycosides. A systematic survey of this sequential double aryl C-glycosidation is described. (C) 1998 Elsevier Science Ltd. AII 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.