52058-11-4

Upstream product

• 64-17-5 ethanol 
• 55-10-7 4-hydroxy-3-methoxy-mandelic acid 
• 50-81-7 ascorbic acid 
• 74-96-4 ethyl bromide 

Downstream Products

• 55-10-7 4-hydroxy-3-methoxy-mandelic acid 
• 854826-84-9 4-hydroxy-3-methoxy-mandelic acid-amide 
• 2034-60-8 1-(4-hydroxy-3-methoxy-phenyl)-propane-1,2-dione 
• 97412-19-6 diacetylvanillylmandelic acid 
• 854671-16-2 1-acetoxy-1-(4-acetoxy-3-methoxy-phenyl)-3-chloro-acetone 
• 854676-35-0 1-acetoxy-1-(4-acetoxy-3-methoxy-phenyl)-3-diazo-acetone 
• 854668-61-4 1,3-diacetoxy-1-(4-acetoxy-3-methoxy-phenyl)-acetone 
• 93904-00-8 ethyl 4-(benzyloxy)-3-methoxymandelate 
• 1415803-96-1 ethyl 2,3,3-tri-(4-hydroxy-3-methoxyphenyl)propanoate 
• 1360605-46-4 4,4',4''-(3-hydroxypropane-1,1,2-triyl)tris(2-methoxyphenol) 
• 1451148-39-2 ethyl 2-(4-(benzyloxy)-3-methoxyphenyl)-2-oxoacetate 
• 1451148-37-0 ethyl 2,3,3-tri(4-benzyloxy-3-methoxyphenyl)prop-2-enoate 
• 1451148-38-1 ethyl 3,3-dibromo-2-(4-benzyloxy-3-methoxyphenyl)prop-2-enoate 
• 97638-21-6 1-(4-benzyloxy-3-methoxyphenyl)ethane-1,2-diol 

Relevant academic research and scientific papers

Preparation of 2,3,3-Triarylacrylic Acid Esters Using Suzuki-Miyaura Coupling Reactions

We report here a new strategy to produce 2,3,3-triarylacrylic acid esters, a class of 1,2,2-triarylethene compounds with an α,β-unsaturated ester functionality. Our approach requires the preparation of a gem-dibromoalkene precursor from an α-keto ester, followed by the installation of two aryl groups by Suzuki-Miyaura coupling reactions on the two C-Br bonds. Many 2,3,3-triarylacrylic acid esters with one, two, or three different aryl groups were obtained with complete regio- and stereocontrol in most cases.

Anti-inflammatory properties of quebecol and its derivatives

Herein we report our results on the anti-inflammatory activity of quebecol, a polyphenolic compound discovered in maple syrup. Bioassays demonstrated that quebecol has an anti-inflammatory effect on LPS-induced NF-κB activation and inhibits the secretion of two pro-inflammatory cytokines, IL-6 and TNF-α. We also prepared and tested precursors of quebecol and its derivatives corresponding to its substructures of interest, with the aim to study the structure-activity relationships. Comparing the results obtained for all tested compounds allowed the identification of the main moiety responsible for the anti-inflammatory activity of quebecol.

Total synthesis of quebecol

We report here the total synthesis of quebecol, a new polyphenolic compound with potential applications recently isolated from maple syrup and produced during the condensation of the tree acer saccharum's sap. The synthetic approach we developed involves, as key steps, the formation of a dibromoalkene from an α-ketoester precursor followed by a double Suzuki-Miyaura reaction to unite the three aromatic rings of the target compound on a tetrasubstituted olefin precursor. Our methodology is an efficient pathway to the target compound and leads the way for future analogs.

Reaction of vanilmandelic acid and 4-Hydroxybenzyl alcohol derivatives with L-ascorbic acid

The interaction between vanilmandelic and L-ascorbic acids led to a cyclopent-2-en-one derivative, whereas the reaction or methyl vanilmandelate with L-ascorbic acid yielded 2-furancarboxylic acid as the major product. The model 3-substituted 4-hydroxybenzyl alcohols and L-ascorbic acid produced ascorbigen-type structures, which easily decarboxylated to give mistures of the corresponding 1-aryl-1-deoxyketoses.