(E)-1-(2,6-dihydroxy-4-[[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy]phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one -Drug Synthesis Database

【结构式】

【分子编号】34295

【品名】(E)-1-(2,6-dihydroxy-4-[[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy]phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one

【CA登记号】

【分子式】C₂₁H₂₂O₁₀

【分子量】434.39968

【元素组成】C 58.06% H 5.1% O 36.83%

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：(VIII)

The condensation of 2,4,6-trihydroxyacetophenone (IV) with tetraacetylbromoglucose (V) by means of NaOH in acetone-water gives tetraacetylphloracetophenone-4-O-glucoside (VI), which is condensed with 4-hydroxybenzaldehyde (VII), by means of KOH in alcohol yielding the chalcone derivative (VIII). Finally, this compound is cyclized and deprotected by a treatment with refluxing aqueous HCl.

参考文献中间体

合成目标

【1】 Zemplen, G.; Bognar, R.; Synthese eines phloracetophenon-glucosids, eines naringenin-glucosids und des p-phlorhizins. Ber 1942, 75, 645-655.
【2】 Castaner, J.; Serradell, M.N.; Aboul-Enein, H.Y.; Naringenin. Drugs Fut 1984, 9, 9, 653-654.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	34293	1-(2,4,6-trihydroxyphenyl)-1-ethanone	480-66-0	C₈H₈O₄	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)	34294	(2R,3R,4S,5R)-6-(4-acetyl-3,5-dihydroxyphenoxy)-4,5-bis(acetoxy)-2-[(acetoxy)methyl]tetrahydro-2H-pyran-3-yl acetate		C₂₂H₂₆O₁₃	详情	详情
(VII)	13433	4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde	123-08-0	C₇H₆O₂	详情	详情
(VIII)	34295	(E)-1-(2,6-dihydroxy-4-[[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy]phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one		C₂₁H₂₂O₁₀	详情	详情

Extended Information