Hybrid molecules continue to maintain their stronghold in the drug market, with over 60% of drug candidates in pharmaceutical industries. The substantial expenses for the development and production of biologically privileged drugs are expected to create opportunities for the developments of hybrid molecule-based drugs. Therefore, we have developed a simple and efficient copper catalyzed approach for the synthesis of a wide range of triazole-linked glycohybrids derived from pyrazolo[1,5-a]pyrimidines. Employing microwave-assisted copper catalyzed approach, we developed a concise route using various 7-O-propargylated pyrazolo[1,5-a]pyrimidines and 1-azidoglycosides. This strategy afforded a series of twenty-seven glycohybrids up to 98% yield with diverse stereochemistry. All achieved within a remarkably shortened time frame. Our investigation extends to the evaluation of anti-cancer potential of these synthesized triazole-linked pyrazolo[1,5-a]pyrimidine based glycohybrids. In-vitro assays against MCF-7, MDA-MB231, and MDA-MB453 cell lines reveal intriguing findings. (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(4-(((5-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-7-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate emerges as a standout with potent anti-cancer activity against MDA-MB231 cells (IC50 = 29.1 µM), while (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(4-(((5-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-7-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate demonstrates exceptional inhibitory effects against MCF-7 cells (IC50 = 15.3 µM). These results align with our docking analysis and structure-activity relationship (SAR) investigations, further validating the in-vitro outcomes. This work not only underscores the synthetic utility of our devised protocol but also highlights the promising potential of these glycohybrids as candidates for further anti-cancer therapeutic exploration.