Small changes in the alkane solvent structure in combination with temperature effects lead to four different conformations of stereoselectively deuterated benzene-1,3,5-tricarboxamides in the aggregated state, affecting the expression of the supramolecular chirality and highlighting the role of the solvent structure in self-assembly processes.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c2cc17284d | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Direct synthesis of enone-hydrazones under solvent free and additive free conditions.
Org Biomol Chem
January 2025
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education; Yunnan Provincial Center for Research & Development of Natural Products; School of Chemical Science and Technology, Yunnan University, Kunming, 650091, P.R. China.
A series of enone-hydrazones were synthesized through the reaction of enaminones with hydrazones under solvent-free, additive-free, and metal-catalyst-free conditions. The target products were obtained in high yields, with outstanding group tolerance, stereoselectivity, and chemical selectivity. In this work, a series of novel enaminone skeleton compounds were synthesized, and deuteration experiments showed that enone-hydrazones have different properties from traditional electron-deficient enketones.
View Article and Find Full Text PDFInterception of Alkynyl Tetracoordinate Borons with Sulfur Electrophiles beyond the Zweifel Pathway.
Angew Chem Int Ed Engl
January 2025
Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian, 350108, China.
Zweifel reaction is a powerful strategy to construct olefins from alkenyl tetracoordinate borons in organoboron chemistry, however, it usually only involves one functional group migration and then undergoes an elimination process affording alkenes or alkynes exclusively. Herein, we disclose several intriguing interception of alkynyl tetracoordinate borons with sulfur electrophiles. Wherein, the substituted benzothiophenes are accessed by consecutive 1,2-migrations and intramolecular electrophilic substitution, meanwhile, the challenging and elusive five/four-membered boracycles are easily assembled, and an approach to alkenyl sulfides with good stereoselectivity was developed as well.
View Article and Find Full Text PDFDesigning chemical systems for precision deuteration of medicinal building blocks.
Nat Commun
October 2024
Department of Chemistry, University of Virginia, Charlottesville, VA, USA.
Methods are lacking that can prepare deuterium-enriched building blocks, in the full range of deuterium substitution patterns at the isotopic purity levels demanded by pharmaceutical use. To that end, this work explores the regio- and stereoselective deuteration of tetrahydropyridine (THP), which is an attractive target for study due to the wide prevalence of piperidines in drugs. A series of d-d tetrahydropyridine isotopomers were synthesized by the stepwise treatment of a tungsten-complexed pyridinium salt with H/D and H/D.
View Article and Find Full Text PDFStereoselective and site-divergent synthesis of C-glycosides.
Nat Chem
December 2024
The Institute for Advanced Studies, Wuhan University, Wuhan, China.
Carbohydrates play important roles in medicinal chemistry and biochemistry. However, their synthesis relies on specially designed glycosyl donors, which are often unstable and require multi-step synthesis. Furthermore, the catalytic and stereoselective installation of arylated quaternary stereocentres on sugar rings remains a formidable challenge.
View Article and Find Full Text PDFSynthesis of a deuterated disaccharide internal standard for LC-MS/MS quantitation of heparan sulfate in biological samples.
Carbohydr Res
November 2024
School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Queensland, 4072, Australia. Electronic address:
High levels of heparan sulfate (HS) are a marker for several mucopolysaccharidosis (MPS) disorders which are lysosomal storage diseases caused by genetic defects in HS-degrading enzymes. Quantitation of HS in biological samples is therefore critical for diagnosis and evaluating the efficacy of new therapies. Herein we present the efficient synthesis of a butylated GlcN-GlcA disaccharide and its deuterated derivative for use as an internal standard in a quantitative mass spectrometry-based assay for analysis of HS following butanolysis.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!