Year: 2024
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide We report a de novo enantioselective synthesis of 2,3,4-trideoxy-2,2,3,3,4,4-hexafluoro- d - glycero -hexopyranose (hexafluorinated d -glucose), an iconic polar hydrophobic glycomimetic. The 12-step synthesis features robust and reproducible chemistry and was achieved by incorporating an asymmetric dihydroxylation step to install the stereogenic center with excellent enantioselectivity (95:5 er ). Virtual enantiopurity (>99.5% ee ) was further reached using a simple crystallization procedure and the absolute confirmation was ascertained by X-ray analysis. The synthetic route also allowed access to the novel hexafluorinated heptose derivative 2,3,4-trideoxy-2,2,3,3,4,4-hexafluoro- l - threo -heptopyranose.
Source: The Journal of Organic Chemistry
Institutions: Ghent University, University of Southampton
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
Awards: Magnetic resonance equipment for advanced material research: molecular characterisation of solid, soft, homogeneous and heterogeneous matter for the development of advanced functional materials and chemical catalysis, G1736942822, Harvesting the potential of fluorine labels and NMR spectroscopy to study the conformation of polyproline sequences and their interaction with biomolecular targets, G2492948467, G2866123656, Fluorinations with implications: enhancing the potential of biologically and medicinally interesting molecules through targeted fluorine introduction, G5200278345, G5254430835, G6244568949, G7875997330, Core Capability for Chemistry Research in Southampton
OpenAlex ID: W4402504146