2-[3,4-bis(benzyloxy)phenyl]-3-hydroxy-4H-chromen-4-one -Drug Synthesis Database

【结构式】

【分子编号】49831

【品名】2-[3,4-bis(benzyloxy)phenyl]-3-hydroxy-4H-chromen-4-one

【CA登记号】

【分子式】C₂₉H₂₂O₅

【分子量】450.49068

【元素组成】C 77.32% H 4.92% O 17.76%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

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.

参考文献中间体

合成目标

【1】 Frederique, A.; et al.; Synthesis of novel 3,7-substituted-2-(3',4'-dihydroxyphenyl) flavones with improved antioxidant activity. J Med Chem 2000, 43, 20, 3752.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	29654	2-hydroxyacetophenone; 1-(2-hydroxyphenyl)-1-ethanone	118-93-4	C₈H₈O₂	详情	详情
(II)	49829	3,4-Dibenzyloxybenzaldehyde; 3,4-Bis(benzyloxy)benzaldehyde	5447-02-9	C₂₁H₁₈O₃	详情	详情
(III)	49830	(E)-3-[3,4-bis(benzyloxy)phenyl]-1-(2-hydroxyphenyl)-2-propen-1-one		C₂₉H₂₄O₄	详情	详情
(IV)	49831	2-[3,4-bis(benzyloxy)phenyl]-3-hydroxy-4H-chromen-4-one		C₂₉H₂₂O₅	详情	详情
(V)	27260	(2R,3R,4S,5S,6R)-4,5-bis(acetoxy)-6-[(acetoxy)methyl]-2-bromotetrahydro-2H-pyran-3-yl acetate	572-09-8	C₁₄H₁₉BrO₉	详情	详情
(VI)	49832	(2R,3R,4S,5R)-3,5-bis(acetoxy)-2-[(acetoxy)methyl]-6-([2-[3,4-bis(benzyloxy)phenyl]-4-oxo-4H-chromen-3-yl]oxy)tetrahydro-2H-pyran-4-yl acetate		C₄₃H₄₀O₁₄	详情	详情

Extended Information