Synthesis of 5-glycosylated β-anhydroicaritine.

Glycosylation plays an important role in many biological processes, and its structural changes have a significant impact on biological activity. Unlike natural icariin, icariside I, and icariside II, a simulated unnatural 5-glycosylation (4) was designed to expand substrate adaptability and the pharmacological properties of the parent compound. Therefore, starting from commercially available icaritin, 5-glycosylated icaritin was successfully synthesized in moderate yield through cyclization, selective 3-alkylation, 5-glycosylation, and hydrogenation steps. The structure was identified by ¹H nuclear magnetic resonance (NMR), ¹³C NMR, MS, and x-ray spectroscopy. [ABSTRACT FROM AUTHOR]