2-(2',3',4'-tri-O-acetyl-6'-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)-1,4-dimethoxynaphthalene | 1093850-39-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2',3',4'-tri-O-acetyl-6'-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)-1,4-dimethoxynaphthalene
• CAS: 1093850-39-5
• 化学式: C₃₀H₄₂O₁₀Si
• 分子量: 590.743
• InChiKey: SISZTUDTOKDOPA-GLOKNNJPSA-N

反应信息

• 作为反应物：
  描述：

  2-(2',3',4'-tri-O-acetyl-6'-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)-1,4-dimethoxynaphthalene 在 Jones reagent 作用下， 以 丙酮 为溶剂， 以78%的产率得到(2S,3S,4R,5S,6S)-3,4,5-triacetoxy-6-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)-tetrahydro-2H-pyran-2-carboxylic acid
  参考文献：
  名称：

  β-C-Glycosiduronic acids and β-C-glycosyl compounds: New PTP1B inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.10.091
• 作为产物：
  描述：

  、 乙酸酐 生成 2-(2',3',4'-tri-O-acetyl-6'-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)-1,4-dimethoxynaphthalene
  参考文献：
  名称：

  β-C-Glycosiduronic acids and β-C-glycosyl compounds: New PTP1B inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.10.091

文献信息

• 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.