The traditional method for attaching sugars to natural products, drugs or drug leads is by chemical glycosylation. This classical approach typically requires multiple protection/deprotection steps in addition to the key anomeric activation/coupling reaction which, depending upon the glycosyl donor/acceptor pair, can lead to a mixture of anomers. Unlike classical chemical glycosylation, glycorandomization methods are divergent (i.e., diverge from a common starting material, see divergent synthesis) and are not dependent upon sugar/aglycon protection/deprotection or sugar anomeric activation. Two complementary strategies to achieve glycorandomization/diversification have been developed: an enzyme-based strategy referred to as chemoenzymatic glycorandomization and a chemoselective method known as neoglycorandomization. Both methods start with free reducing sugars and a target aglycon to afford a library of compounds which differ solely by the sugars appended to the target natural product, drug or drug lead.