Synthesis of glycyrrhizin analogues containing fluorinated beta(1-->2)-linked disaccharides.
For studies on the recognition mechanisms for Glycyrrhizin-induced biological activities, seven Glycyrrhizin analogues with 3'-, 4'-, 6'-, 3-, and 4-fluorinated 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoses (1-5) and 3- and 4-fluorinated 2-O-beta-D-glucopyranuronosyl-beta-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 beta-glycosylation of methyl glycyrrhetate, promoted with trimethylsilyl trifluoromethanesulfonate.
Morishima
N
N
School of Nursing, Kitasato University, Sagamihara, Japan.
Mori
Y
Y
D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry; D006034:Glycyrrhetinic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D019695:Glycyrrhizic Acid; D009682:Magnetic Resonance Spectroscopy
D004187:Disaccharides; D005461:Fluorine; D019695:Glycyrrhizic Acid; D006034:Glycyrrhetinic Acid