The aim of this work was the regioselective synthesis of 1,4-disubstituted 1,2,3-triazole L-ascorbic acid derivatives (3 – 8) with potential antitumor activity. For this purpose, 6-O-tosyl-2,3-O,O-dibenzyl-L-ascorbic acid (1) was prepared and then converted to the corresponding azido derivative of L-ascorbic acid (2). 1,2,3-Triazole derivatives of L-ascorbic acid (3 – 8) were prepared by microwave assisted 1,3-dipolar cycloaddition reaction of the azide (2) and corresponding terminal alkynes with Cu(I), as a catalyst, based on the concept of "click" chemistry. In order to obtain better overall yield of target compounds, two synthetic pathways were used. First pathway includes the conversion of the tosylated L-ascorbic acid derivative (1) to the azide (2), its isolation and then a "click" reaction of the azide (2) and corresponding alkynes to form 1,4-disubstituted 1,2,3-triazole L-ascorbic acid derivatives (3 – 8). Second synthetic pathway was a tandem reaction in which the azido derivative (2) was not isolated, but was formed in situ from the tosylated derivative (1) and via reaction with the corresponding alkynes 1,4-disubstituted 1,2,3-triazole derivatives of L-ascorbic acid (3, 5) were obtained. In order to explore the antioxidant properties of the 1,2,3-triazole L-ascorbic acid derivatives, compound with free hydroxyl groups (9) was prepared by removal of the benzyl protecting groups. The structures of all compounds have been confirmed by 1H and 13C NMR spectroscopy.