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【结 构 式】 
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【药物名称】Frederine 【化学名称】2-(3,4-Dihydroxyphenyl)-3-(D-glucopyranosyloxy)-4H-1-benzopyran-4-one 【CA登记号】307521-67-1, 199469-77-7 ((S)-isomer) 【 分 子 式 】C21H20O10 【 分 子 量 】432.38755 |
【开发单位】Universiteit Maastricht (Originator), Vrije Universiteit (Originator) 【药理作用】Chemoprotective Agents, ONCOLYTIC DRUGS, Antioxidants |
合成路线1
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.
| 【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 |