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Updated: Jun 17, 2025

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
Published on: September 6, 2019
A concise synthetic approach for isoiminosugars
Martin Thonhofer1, André Culum1, Tobias Dorn1
1Graz University of Technology, Institute of Chemistry and Technology of Biobased Systems, Stremayrgasse 9, A-8010, Graz, Austria.
Abstract:
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.
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