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Updated: Oct 18, 2026

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
Published on: September 6, 2019
Stereoselectivity in the synthesis of unnatural disaccharides
L Kniezo1, M Budĕsínský, P Vojtísek
1Department of Chemistry of Natural Compounds, Institute of Chemical Technology, Prague, Czech Republic. Ladislav.Kniezo@vscht.cz
Abstract:
The synthesis of branched-chain sugars with two hexose moieties linked by a -CH2- bridge in the positions (3-->3) is described. The synthesis starts from protected 3-deoxy-3-(formylmethyl)-alpha-D-allofuranose in which the original formyl group is converted in four reaction steps into a new hexopyranose of D- or L-configuration. The relative configuration of the prepared compounds was determined on the basis of coupling constants in the 1H NMR spectra whereas the absolute configuration of the newly created pyranose was unequivocally assigned by single crystal X-ray crystallography of the 3-deoxy-3-[(2R,4R,5S,6R)-2-ethoxy-5-acetoxy-6- acetoxymethyl-tetrahydropyran-4-ylmethyl]-1,2:5,6-di-O-isopropylid ene- alpha-D-allofuranose (10).
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