Synthesis of flavonoid glycosides. III. Synthesis and tastes of some flavanone- and dihydrochalcone glycosides.

Naringenin-7-β-maltoside (I), -7-β-cellobioside (II), -7-β-lactoside (III), -7-β-melibioside (IV) and hesperetin-7-β-[D-galactosyl (α 1→2) D-glucoside] (V), -7-β-[D-glucosyl (β 1→2) D-galactoside] (VI) and -7-β-melibioside (VII) were prepared by the coupling of naringenin or hesperetin with the acetobromo derivatives of appropriate disaccharides followed by removal of the protecting acetyl groups. Narigenindihydrochalcone-4'-β-kojibioside (VIII), -4'-β-maltoside (IX), -4'-β-cellobioside (X), -4'-β-lactoside (XI), -4'-β-melibioside (XII) and hesperetindihydrochalcone-4'-β-[D-galactosyl (α 1→2) D-glucoside] (XIII), -4'-β-sophoroside (XIV) and -4'-β-melibioside (XV) were synthesized by catalytic reduction of the appropriate flavanone-7-β-glycosides. Among the compounds synthesized, IX and X are 4 and 8 times as sweet as sucrose on the basis of percentage concentration, respectively, but the others are tasteless.