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【结 构 式】

【药物名称】

【化学名称】2,4-Dihydroxy-3,6-dimethylbenzoic acid 4-(ethoxycarbonyl)-3-hydroxy-2,5-dimethylphenyl ester

【CA登记号】

【 分 子 式 】C20H22O7

【 分 子 量 】374.39414

【开发单位】Universität Regensburg (Originator), Westfälische Wilhelms-Univ. Münster (Originator)

【药理作用】Antipsoriatics, DERMATOLOGIC DRUGS, Leukotriene Synthesis Inhibitors

合成路线1

Ethyl ester (II) is alkylated with benzyl chloride (I) by means of K2CO3 in acetone to yield 4-benzyloxy derivative (III), which is then hydrolyzed with KOH in H2O/DMSO to provide carboxylic acid (IV). Depside formation between derivative (IV) and ethyl ester (II) by means of trifluoroacetic anhydride in toluene furnishes ethyl benzoate derivative (V), which is finally hydrogenated over Pd/C in AcOEt to yield the target product.

1 Kumar, S.; Muller, K.; Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth. 1.Novel analogues of barbatic and diffractaic acid. Eur J Med Chem 1999, 34, 12, 1035.
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) 19171 1-(Chloromethyl)benzene; Benzyl chloride 100-44-7 C7H7Cl 详情 详情
(II) 47148 ethyl 2,4-dihydroxy-3,6-dimethylbenzoate C11H14O4 详情 详情
(III) 47149 ethyl 4-(benzyloxy)-2-hydroxy-3,6-dimethylbenzoate C18H20O4 详情 详情
(IV) 47150 4-(benzyloxy)-2-hydroxy-3,6-dimethylbenzoic acid C16H16O4 详情 详情
(V) 47151 ethyl 4-[[4-(benzyloxy)-2-hydroxy-3,6-dimethylbenzoyl]oxy]-2-hydroxy-3,6-dimethylbenzoate C27H28O7 详情 详情
Extended Information