A concise synthetic approach for isoiminosugars

• Published in: Carbohydrate research Vol. 544; p. 109239
• Main Authors: Thonhofer, Martin, Culum, André, Dorn, Tobias, Fischer, Roland, Prasch, Herwig, Stütz, Arnold E., Weber, Patrick, Wrodnigg, Tanja M.
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier Ltd 01.10.2024
• Subjects: 4-epi-isofagomine; beta-Galactosidase - antagonists & inhibitors; beta-Galactosidase - chemistry; beta-Galactosidase - metabolism; Enzyme Inhibitors - chemical synthesis; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - pharmacology; Glycosid hydrolases; Imino Pyranoses - chemical synthesis; Imino Pyranoses - chemistry; Imino Sugars - chemical synthesis; Imino Sugars - chemistry; Inhibitor; Isoiminosugar; Stereoisomerism; Synthesis; Isoiminosugar; Inhibitor; Synthesis; Glycosid hydrolases; 4-epi-isofagomine
• ISSN: 0008-6215; 1873-426X; 1873-426X
• DOI: 10.1016/j.carres.2024.109239

Isoiminosugars are highly biological active substances. Herein, we report a concise synthetic approach for this class of compounds. The key step relies on a stereospecific 1,2-hydride shift in O-2 tosylated glycopyranosides leading to C-2 branched glycofuranosides. This approach enables a 4-step synthesis of powerful β-galactosidase inhibitor 4-epi-isofagomine starting from a simple d-glucopyranoside. [Display omitted] •Isoiminosugars are powerful tools in the broad field of glycosciences.•One synthetic method: from common d-glucosides to powerful β-galactosidase inhibitors.•A general and concise synthetic approach for isoiminosugars.•Access to 4-epi-isofagomine in 4 simple synthetic steps.