Issue 16, 2025

NHC-catalysed synthesis of hydroxy methylene-bridged formyl-di-xylofuranose: access to tetrakis and spiro tricyclic xylofuranose

Abstract

Herein, the role of N-heterocyclic carbenes (NHC) as a Brønsted base in the transformation of xylofuranose aldehyde has been explored. Furanose aldehyde undergoes intermolecular self-condensation catalyzed by thiazolium-derived carbene, producing hydroxy methylene-bridged formyl-di-xylofuranose retaining the C-4 aldehyde. Furthermore, modification of the hydroxy methylene-linked disaccharide yields spiro[furano-4,5-pyrano[3,2-b]furanose] and oxy-methylene-bridged di-formyl-xylofuranose cyclic tetrasaccharide.

Graphical abstract: NHC-catalysed synthesis of hydroxy methylene-bridged formyl-di-xylofuranose: access to tetrakis and spiro tricyclic xylofuranose

Supplementary files

Article information

Article type
Communication
Submitted
13 Feb 2025
Accepted
17 Mar 2025
First published
18 Mar 2025

Org. Biomol. Chem., 2025,23, 3824-3829

NHC-catalysed synthesis of hydroxy methylene-bridged formyl-di-xylofuranose: access to tetrakis and spiro tricyclic xylofuranose

N. Sakander, R. Haldar and D. Mukherjee, Org. Biomol. Chem., 2025, 23, 3824 DOI: 10.1039/D5OB00259A

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