Frederine

Chemical Name: 2-(3,4-Dihydroxyphenyl)-3-(D-glucopyranosyloxy)-4H-1-benzopyran-4-one
CAS No. 307521-67-1, 199469-77-7 ((S)-isomer)
项目整合开发状态: Preclinical
项目研究机构: Universiteit Maastricht (Originator), Vrije Universiteit (Originator)
合成路线:Claisen condensation between 2'-hydroxyacetophenone (I) and 3,4-dibenzyloxybenzaldehyde (II) afforded chalcone (III) which was further subjected to the Agar-Flynn-Oyamada reaction to give flavonol (IV).The silver oxide-assisted glycosylation of (IV) with acetobromoglucose (V) in pyridine furnished the protected glucoside (VI).Removal of the acetyl protecting groups of (VI) was effected by methanolysis in the presence of potassium tert-butoxide to yield (VII).Subsequent catalytic hydrogenolysis of the benzyl groups of (VII) provided the title compound.