Glycosyl 3-Phenyl-4-pentenoates as Versatile Glycosyl Donors: Reactivity and Their Application in One-Pot Oligosaccharide Assemblies

Both glycoconjugates and oligosaccharides are important biomolecules having significant roles in several biological processes, and a new strategy for their synthesis is crucial. Here, we report a versatile N-iodosuccinimide/trimethylsilyl triflate (NIS/TMSOTf) promoted glycosidation approach with shelf-stable 3-phenyl-4-pentenoate glycosyl as a donor for the efficient synthesis of O/C-glycosides with free alcohols, silylated alcohols, and C-type nucleophile acceptors in good to excellent yields. The mild activation conditions and outstanding reactivity of phenyl substituted pentenoate donors analogous to 4-pentenoate glycosyl donors enhance their applicability to various one-pot strategies for the synthesis of oligosaccharides, such as single-catalyst one-pot and acceptor reactivity-controlled one-pot strategies.