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.