Glycohybrids are biologically significant molecules with variety of biological functions and are found as structural motifs in numerous natural products. Here, we report the synthesis of various new coumarin-based O-glycoconjugates as glycohybrids that are chirally enriched and bridged by 1,2,3-triazoles ring system. The1,2,3-triazoles bridging was done via CuAAC click-chemistry. Click chemistry offers several advantages, including high chemo- and regioselectivity, mild reaction conditions, easy purification, and compatibility with multiple functional groups. Two series of O-glycoconjugates as new glycohybrids were designed and efficiently synthesized in very good isolated yields, using d-glucose, d-galactose, d-mannose, d-arabinose, 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal and 3,4-di-O-acetyl-D-arabinal derived 1-O-propargylated glycosides, reacting with various 4-azidocoumarins under click-chemistry reaction conditions. The prepared new coumarin-based O-glycoconjugates as glycohybrids were found to possess anticancer activity against MCF-7 breast cancer cell lines at micromolar concentration.