Efficient Two Step b-Glycoside Synthesis from N-Acetyl d-Glucosamine: Scope and Limitations of Copper(II) Triflate-Catalyzed Glycosylation

摘要

β-Linked glycosides of N-acetyl glucosamine are widespread in nature. Their direct synthesis is hampered by the low reactivity of GlcNAc as a glycosyl donor. We report a selective and rapid copper(II) triflate-catalyzed two-step synthesis of β-glycosides of GlcNAc from cheap GlcNAc as starting material without purification of intermediates. α-Specific glycosylation can be achieved by increasing the amount of catalyst and extending reaction times.