Synthesis of glycyrrhizin analogues containing fluorinated β(1→2)-linked disaccharides Original Research Article

For studies on the recognition mechanisms for Glycyrrhizin-induced biological activities, seven Glycyrrhizin analogues with 3′-, 4′-, 6′-, 3-, and 4-fluorinated 2-O-β-d-glucopyranosyl-β-d-glucopyranoses (1–5) and 3- and 4-fluorinated 2-O-β-d-glucopyranuronosyl-β-d-glucopyranoses (6 and 7) were synthesized through a stepwise glycosylation procedure. 1,2-Di-O-acetyl-4,6-di-O-benzyl-3-deoxy-3-fluoro- (13) and 1,2-di-O-acetyl-3,6-di-O-benzyl-4-deoxy-4-fluoro-d-glucopyranose (14) were employed for the first β-glycosylation of methyl glycyrrhetate, promoted with trimethylsilyl trifluoromethanesulfonate.