3-tert-butyldimethylsilyloxy-4,5-(diphenylmethylenedioxy)benzoic acid | 146300-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-tert-butyldimethylsilyloxy-4,5-(diphenylmethylenedioxy)benzoic acid
• 英文别名: 7-[Tert-butyl(dimethyl)silyl]oxy-2,2-diphenyl-1,3-benzodioxole-5-carboxylic acid
• CAS: 146300-70-1
• 化学式: C₂₆H₂₈O₅Si
• 分子量: 448.591
• InChiKey: LXYNOOMDLWKPMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-tert-butyldimethylsilyloxy-4,5-(diphenylmethylenedioxy)benzoic acid 在 palladium on activated charcoal 4-二甲氨基吡啶 、 四丁基氟化铵 、 氢气 、 4-(dimethylamino)pyridine hydrochloride 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 methyl 2,3-di-O-galloyl-α-D-glucopyranoside
  参考文献：
  名称：

  O-Methylglucogalloyl esters: Synthesis and evaluation of their antimycotic activity

  摘要：

  The two anomers of O-methyl gluco-2,3-digalloyl esters were synthesized and their antimycotic activity toward yeasts of biomedical importance was evaluated. When used at subinhibitory concentration and regardless of stereochemistry at the anomeric carbon, these compounds enhance the antimycotic activity of Amphotericin B. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.037
• 作为产物：
  描述：

  二氯二苯甲烷 在 lithium hydroxide 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-tert-butyldimethylsilyloxy-4,5-(diphenylmethylenedioxy)benzoic acid
  参考文献：
  名称：

  O-Methylglucogalloyl esters: Synthesis and evaluation of their antimycotic activity

  摘要：

  The two anomers of O-methyl gluco-2,3-digalloyl esters were synthesized and their antimycotic activity toward yeasts of biomedical importance was evaluated. When used at subinhibitory concentration and regardless of stereochemistry at the anomeric carbon, these compounds enhance the antimycotic activity of Amphotericin B. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.037

文献信息

• Gallotannins and ellagitannins as regulators of cytokine release
  申请人：The Penn State Research Foundation

  公开号：US07288273B1

  公开（公告）日：2007-10-30

  A means and method for increasing or inhibiting the secretion of cytokines using gallotannins and ellagitannins is described. The preferred cytokine release inhibiting compounds are dimeric gallotannins having a linker molecule that misaligns the carbohydrate cores of the compounds. The preferred cytokine release promoting gallotannins and ellagitannins include a diaryl ether linker unit. In comparison to the more structurally complex ellagitannins, the compounds of this invention are structurally simpler, easier to synthesize, and more potent.

  描述了一种使用没食子单宁和鞣花单宁增加或抑制细胞因子分泌的方法和手段。首选的细胞因子释放抑制化合物是具有连接分子的二聚没食子单宁，该连接分子使化合物的碳水化合物核心错位。首选的促进细胞因子释放的没食子单宁和鞣花单宁包括二芳基醚连接单元。与结构更复杂的鞣花单宁相比，本发明的化合物结构更简单、更容易合成且更有效。
• Gallotannins and Tannic Acid: First Chemical Syntheses and In Vitro Inhibitory Activity on Alzheimer’s Amyloid β-Peptide Aggregation
  作者：Tahiri Sylla、Laurent Pouységu、Grégory Da Costa、Denis Deffieux、Jean-Pierre Monti、Stéphane Quideau

  DOI：10.1002/anie.201411606

  日期：2015.7.6

  against Alzheimer’s disease has unveiled several plant polyphenols that are capable of inhibiting the formation of toxic β‐amyloid fibrils. Gallic acid based gallotannins are among these polyphenols, but their antifibrillogenic activity has thus far been examined using “tannic acid”, a commercial mixture of gallotannins and other galloylated glucopyranoses. The first total syntheses of two true gallotannins

  在寻找对抗阿尔茨海默氏病的新先导化合物的过程中，对天然产物的筛选揭示了几种能够抑制有毒β-淀粉样蛋白原纤维形成的植物多酚。在这些多酚中有基于没食子酸的没食子鞣质，但是迄今为止，已经使用“鞣酸”（一种鞣花酸和其他没食子酰化吡喃葡萄糖的商业混合物）检查了它们的抗原纤维形成活性。现在描述两种真实的没食子鞣质，六没食子酰基吡喃葡萄糖和十加铝基化的化合物的首次总合成，该化合物的结构通常用于描绘“鞣酸”。这些去甲没食子鞣质和更简单的没食子酸酯化的葡萄糖衍生物均在体外抑制淀粉样蛋白β肽（Aβ）的聚集，并且单没食子酸酯化的α-葡糖醇和天然β-六没糖基葡萄糖被证明是最强的抑制剂。
• Ellagitannin Chemistry. The First Total Chemical Synthesis of an Ellagitannin Natural Product, Tellimagrandin I
  作者：Ken S. Feldman、Susan M. Ensel、Robert D. Minard

  DOI：10.1021/ja00084a015

  日期：1994.3

  Tellimagrandin I was synthesized by two different biogenetically patterned routes. One route featured diastereoselective galloyl ester coupling between the O(4) and O(6) galloyl moieties in a glucose-derived substrate bearing additional protected galloyl groups on 0(2) and 0(3). The second route relied on a completely diastereoslective and regioselective Pb(OAc) 4 -based oxidative coupling exclusively

  Tellimagrandin I 是通过两种不同的生物遗传学模式合成的。一种路线的特色是在葡萄糖衍生底物中的 O(4) 和 O(6) 没食子酰部分之间的非对映选择性没食子酰酯耦合，在 0(2) 和 0(3) 上具有额外的受保护没食子酰基团。第二种途径依赖于完全非对映选择性和区域选择性的基于 Pb(OAc) 4 的氧化偶联，仅在葡萄糖衍生底物中的 O(4) 和 O(6) 没食子酰酯之间进行氧化偶联，该底物具有 O(2)- O(6)。基于分子力学的构象分析为观察到的选择性提供了依据
• Ellagitannin Chemistry. First Total Synthesis of the 2,3- and 4,6-Coupled Ellagitannin Pedunculagin
  作者：Ken S. Feldman、Randall S. Smith

  DOI：10.1021/jo952130+

  日期：1996.1.1

  The biomimetic synthesis of pedunculagin (1) was accomplished through the sequential diastereoselective formation of two biphenyl C-C bonds. The synthesis strategy employed is predicated on extensive conformational modeling and involves initial oxidative coupling of the galloyl moieties at the O(2) and O(3) positions of an appropriately protected glucose-derived core, followed by installation and oxidative

  pedunculagin（1）的仿生合成是通过连续两个非对映选择性形成两个联苯CC键来完成的。所采用的合成策略基于广泛的构象模型，涉及在适当保护的葡萄糖衍生核心的O（2）和O（3）位置上的没食子酰基部分的初始氧化偶联，然后在没食子酸酯安装和氧化偶联没食子酸酯O（4）和O（6）位置。
• Ellagitannin Chemistry. Syntheses of Tellimagrandin II and a Dehydrodigalloyl Ether-Containing Dimeric Gallotannin Analogue of Coriariin A
  作者：Ken S. Feldman、Kiran Sahasrabudhe

  DOI：10.1021/jo9816966

  日期：1999.1.1

  The first chemical synthesis of the naturally occurring ellagitannin tellimagrandin II is reported. Key steps of the synthesis include the atropselective oxidative coupling of suitably protected galloyl rings at the O(4) and O(6) positions of a glucopyranose core, and the stereoselective acylation of the derived anomeric alcohol with a galloyl chloride. In addition, the synthesis of a novel gallotannin-ellagitannin

  天然存在的鞣花单宁tellimagrandin II的首次化学合成已有报道。合成的关键步骤包括在吡喃葡萄糖核心的O（4）和O（6）位置适当保护的没食子酰基环的atropselective氧化偶联，和衍生的异头醇与没食子酰氯的立体选择性酰化。另外，描述了新的没食子鞣质-鞣花单宁杂交体的合成。该二聚体构建体依赖于杂Diels-Alder环加成/还原性重排序列，以从基于单体五烷基酰葡萄糖的邻醌递送完整骨架。