88208-98-4Relevant academic research and scientific papers
Tailoring Reaction Selectivity by Modulating a Catalytic Diad on a Foldamer Scaffold
Andrews, Mary Katherine,Gellman, Samuel H.,Liu, Xinyu
supporting information, (2022/02/10)
Use of a tunable molecular scaffold to align a reactive diad for bifunctional catalysis can reveal relationships between functional group identity and reactivity that might otherwise be impossible to identify. Here we use an α/β-peptide helix to show that an aligned pair of primary amine groups is uniquely competent to catalyze crossed aldol condensations with an aryl aldehyde as the electrophile. Geometrically similar diads in which one amine group is secondary, or both are secondary, are good catalysts for other types of aldol condensations but not those involving an aryl aldehyde. Catalytic efficacy requires β-amino acid residues that are preorganized for helix formation via cyclic constraint. Conventional peptides (exclusively α-amino acid residues) that display the primary amine diad are poor catalysts, which highlights the critical role of the foldamer scaffold.
An expedient synthesis of 5-n-alkylresorcinols and novel 5-n-alkylresorcinol haptens
Parikka, Kirsti,Waehaelae, Kristiina
supporting information; experimental part, (2010/04/22)
The first synthesis of bioactive long alkyl chain 5-n-alkylresorcinols, present in whole grain products, by a novel modification of the Wittig reaction is described. All the main long chain 5-n-alkylresorcinols present in rye and wheat, including C23 and C25 analogues and haptens, which have not been previously prepared, were synthesised. Microwave-promoted reactions of a semistabilized ylid and alkanals in water gave good yields in both pressurized and open systems. An alternative microwave-promoted synthesis starting from non-stabilized alkyltriphenylphosphonium salts and 3,5-dimethoxybenzaldehyde worked as well. Aqueous media were suitable for the reactions even if the starting materials were not soluble in water. The 5-n-alkylresorcinols are potential biomarkers of whole grain intake, and the new hapten derivatives of 5-n-alkylresorcinols will open the way for the immunochemical detection techniques of alkylresorcinols.
Synhtesis of Some Aromatic Prostaglandin Analogues. Part 1
Durrant, Graham,Green, Richard H.,Lambeth, Paul F.,Lester, Michael G.,Taylor, Nigel R.
, p. 2211 - 2214 (2007/10/02)
7-heptanoic acid (4) has been prepared in six steps from 3,5-dimethoxybenzaldehyde.
