2-Deoxy-2-fluoro-d-glucose, 3-deoxy-3-fluoro-d-glucose and 6-deoxy-6-fluoro-d-glucose were converted into the corresponding maltose derivatives using Arabidopsis thaliana DPE2-mediated trans-glycosylation reaction with glycogen acting as a glucosyl donor. 19F NMR spectroscopy proved to be a valuable tool for monitoring the progress of these reactions and to assess the nature of resulting oligomeric products.