Reaction mixtures were loaded onto a silica column that had been pre-treated with triethylamine where nonpolar impurities were washed off with hexanes and products were eluted by increasing the polarity of the mobile phase with ethyl acetate. Further, cycloaddition reactions showed a propensity to go to near completion, with yields in the 80% range, leaving few impurities to remove from the crude reaction mixtures. Amide and sulfonamide analogs were also prepared from aminoethyl glycoside 4 via acylation reactions. Using an amino functionalized PGD precursor was logical because it was accessible from the azido compound and it could be diversified directly to yield amides or sulfonamides, respectively. Treatment of the amines with acid chlorides in the presence of a base gave rise to amide products 10a-c, in varying yields (Table ). Sulfonamide 10d was prepared from amine 4 and phenylsulfonyl chloride in a similar manner. Purifications were carried out in the same manner as other diversification sequences with normal phase chromatography using gradient elution. The extensive scope and reliability of palladium catalyzed coupling reactions guided us towards the Suzuki reaction as an additional avenue for diversifying desosamine. Palladium mediated couplings tend to play a prominent role in medchem campaigns and reliably allow for the incorporation of aromatic and heteroaromatic moieties that can modulate target binding. A common set of reaction conditions were identified and then utilized to prepare the compounds in Table . The procedure entailed heating a mixture of the appropriate desosaminyl glycoside containing an aryl bromide on its aglycone (i.e, 5 or 6) and boronic acid/boronic ester in the presence of Cs 2 CO 3 and Pd(Cl) 2 (PPh 3 ) 2 in a dioxane/water mixture. Purification of products in this series was once again facilitated by their tendency to be retained under normal phase silica chromatography with low polarity solvents. Increasing the polarity eluted the compounds with little contamination. The meta-substituted benzyl glycoside 5 yielded biaryl analogs 11a-f. Similarly, para-substituted glycoside 6 gave rise to biaryls 12a-f; yields were largely consistent over the couplings that were conducted. The boronic acids/esters were chosen to vary the size, electronics, substitution, or heteroatoms on the aromatics attached onto the aglycone.