PGD is a viable platform for assembling glycosylated small molecule libraries that can be evaluated for activity in biochemical and biological screens. Late-stage diversifications on the aglycones of functionalized desosaminyl glycosides via cyloadditions, acylations, and Suzuki couplings reported here constitute proof-of-concept of the PGD method. It leverages the investment of an early stage glycosylation reaction toward a pay-off that delivers individual compounds through straightforward, chemoselective reactions in library synthesis. A variety of reactive handles, in addition to those demonstrated here, should be amenable to the PGD approach. A potential drawback is that unprotected sugars, which are the preferred PGD precursors, may be poorly soluble in organic solvents or give rise to unwanted side products under the conditions of a given diversification reaction. Many click reactions, however, tolerate aqueous reaction conditions, or they can be optimized to overcome solubility and selectivity challenges. Compounds from our small PGD library showed weak inhibition of protein synthesis in an in vitro transcription-translation assay using E. coli ribosomes. Inhibitory compounds also showed antibacterial activity again Gram positive and Gram negative bacteria. Also, one library member inhibited T-cell activation in a cell-based assay. The assay results demonstrate two pathways that are enabled by access to PGD libraries. In one, sugars with known binding interactions with a target can be leveraged as an anchoring fragment in a discovery campaign. In the other, PGD library compounds are screened in high content assays in a target agnostic fashion. In either scenario, further SAR or medchem of interesting compounds should be tractable based on the strategy used for their synthesis.