(-)-Epigallocatechin gallate, (-)-EGCG, Teavigo

(-)-表没食子儿茶素没食子酸酯Chemical Name: 3,4,5-Trihydroxybenzoic acid (2R-cis)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl ester; (-)-Epigallocatechin 3-O-gallate; (-)-3-O-Galloylepigallocatechin
CAS No. 989-51-5
项目整合开发状态: Phase III
项目研究机构: National Cancer Institute (Not Determined), University of California, San Francisco (Not Determined)
合成路线:An enantioselective synthesis of epigallocatechin-3-gallate has been reported: The condensation of 3,4,5-tris(benzyloxy)cinnamyl alcohol (I) with 3,5-bis(benzyloxy)phenol (II) by means of H2SO4 gives the diphenylpropene derivative (III),which is silylated with TBDMS-Cl and imidazole to yield the silyl ether (IV).The asymmetric dihydroxylation of (IV) with AD-mix-alpha affords diol (V),which is desilylated with TBAF in THF providing the trihydroxy compound (VI).Esterification of (VI) with triethyl orthoformate and pyridinium p-toluenesulfonate (PPTS) at room temperature gives the cyclic orthoester (VII),which is treated with the same reactants at 60 癈 to yield the benzopyran (VIII).Compound (VIII) can also be obtained directly from (VI) by treatment with triethyl orthoformate and PPTS at 60 癈.The hydrolysis of the formate group of (VIII) with K2CO3 in methanol affords alcohol (IX),which is oxidized to the corresponding ketone (X) with Dess-Martin periodinane (DMP) in dichloromethane.The reduction of (X) with L-Selectride in THF provides the chiral cis-alcohol (XI),which is esterified with 3,4,5-tris(benzyloxy)benzoyl chloride (XII) and DMAP in dichloromethane giving rise to the protected ester (XIII).Finally,this compound is debenzylated by hydrogenation with H2 over Pd/C in methanol/THF.