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Stereoselective 1,1'-glycosylation reactivity tuning with protecting groups.
Org Biomol Chem
January 2025
Department of Chemistry, University of Natural Resources and Life Sciences, Muthgasse 18, Vienna, A-1190 Austria.
Chemical 1,1'-glycosylation for the synthesis of non-reducing disaccharides is complicated by the need to simultaneously control the stereochemistry at two anomeric centers. While considerable progress has been made in the synthesis of α,α-disaccharides, the assembly of 1,1'-β,β- and 1,1'-β,α-linked non-reducing sugars has received comparatively less attention. Many naturally occurring non-reducing disaccharides and their biologically active mimetics feature asymmetrically located functional groups at different positions on the two pyranose rings, highlighting the demand for reliable stereoselective methods to synthesize fully orthogonally protected 1,1'-conjugated sugars suitable for targeted functionalisation to create important biomolecules.
View Article and Find Full Text PDFThe synthesis of higher-carbon sugar alcohols via indium-mediated acyloxyallylation as potential phase change materials.
Monatsh Chem
December 2023
Institute of Applied Synthetic Chemistry, TU Wien, Vienna, Austria.
Unlabelled: In recent years, sugar alcohols have gained significant attention as organic phase change materials (PCMs) for thermal energy storage due to their comparably high thermal storage densities up to 350 J/g. In a computational study, outstandingly high values of up to ~ 450-500 J/g have been postulated for specific higher-carbon sugar alcohols. These optimized structures feature an even number of carbon atoms in the backbone and a stereochemical configuration in which all hydroxyl groups are in an 1,3--relationship, as found in the natural hexitol d-mannitol.
View Article and Find Full Text PDFSynthesis of Atropisomeric Quinazolin-4-one Derivatives Based on Remote H/D and C/C Discrimination.
J Org Chem
January 2025
Chemistry and Materials Program, College of Engineering, Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan.
Both enantiomers of 2-ethylquinazolin-4-ones bearing -CHO/CDO and CHO/CHO phenyl groups at the N3 position were prepared. These are isotopic atropisomeric compounds based on a remote and conformationally flexible H/D and C/C discrimination, and it was found that a CHCl solution of -CHO/CDO derivative shows a slight specific optical rotation. Furthermore, diastereomeric quinazolinone derivatives bearing a chiral carbon were prepared, and their stereochemical purities and rotational stability as well as the isotopic atropisomerism were verified by H NMR and chiral high-performance liquid chromatography (HPLC) analyses.
View Article and Find Full Text PDFStereochemical Activity and Luminescence Mechanism in (CHN)SnCl Doped with ns Metal Ions.
Inorg Chem
December 2024
State Key Laboratory of Featured Metal Materials and Life-cycle Safety for Composite Structures, School of Physical Science and Technology, Guangxi University, Nanning 530004, China.
Metal halide luminescent materials, particularly those doped with ns ions, exhibit exceptional optical properties. However, the luminescent mechanisms associated with the stereochemical activity of lone-pair electrons remain insufficiently explored. In this study, zero-dimensional (0D) tin-based halide (CHN)SnCl is utilized as a model system to investigate the effects of lattice distortion and lone-pair electron expression on fluorescence emission characteristics by doping with 6s and 5s ions.
View Article and Find Full Text PDFRational Design and Controlled Synthesis of High-Performance Inorganic Short-Wave UV Nonlinear Optical Materials.
Acc Chem Res
January 2025
College of Chemistry, Sichuan University, Chengdu 610065, P. R. China.
Article Synopsis
- The invention of lasers and inorganic second-order nonlinear optical (NLO) crystals has revolutionized technology by enabling unique frequency conversions, essential for various applications including information transmission and industrial uses.
- As the demand for shorter wavelengths and higher precision lasers increases, there is a pressing need for high-performance ultraviolet NLO materials, especially those with wavelengths less than 300 nm.
- Current methods of discovering these materials are often inefficient and based on trial-and-error; therefore, a three-step strategy is proposed for a more rational design, focusing on screening new functional groups, regulating crystal structures, and optimizing synthesis to meet stringent performance criteria.
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