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药物详细合成路线

Name (-)-Epigallocatechin gallate;(-)-EGCG
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 989-51-5
Related CAS
Formula C22H18O11
Structure
Formula Weight 458.38216
Stage III 期临床
Company National Cancer Institute (Not Determined), University of California, San Francisco (Not Determined)
Activity/Mechanism Actinic Keratoses, Agents for, Agents for Liver Fibrosis, Chemopreventive Agents, Dermatologic Drugs, GASTROINTESTINAL DRUGS, Liver and Biliary Tract Disorders, Treatment of, ONCOLYTIC DRUGS, Angiogenesis Inhibitors, Antioxidants, AP-1 Inhibitors, beta-Secretase (BACE) Inhibitors, Fatty Acid Synthase Inhibitors, NF-kappaB (NFKB) Activation Inhibitors, PDGFR Inhibitors, Telomerase Inhibitors, VEGFR Inhibitors, VEGFR-2 (FLK-1/KDR) Inhibitors
Syn. Route 1
Route 1
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 °c to yield the benzopyran (viii). compound (viii) can also be obtained directly from (vi) by treatment with triethyl orthoformate and ppts at 60 °c. 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.
List of intermediates No.
tert-butyl 4-(tributylstannyl)-3,6-dihydro-1(2h)-pyridinecarboxylate (xii)
2-(2,6-dichlorophenyl)-2-(6-methyl-3-pyridazinyl)acetonitrile (i)
2,4-difluorobenzenethiol; 2,4-difluorophenylhydrosulfide (ii)
2-(2,6-dichlorophenyl)-2-{6-[(2,4-difluorophenyl)sulfanyl]-3-pyridazinyl}acetonitrile (iii)
2-(2,6-dichlorophenyl)-2-{6-[(2,4-difluorophenyl)sulfanyl]-3-pyridazinyl}acetamide (iv)
(v)
ethyl 2-{[tert-butyl(diphenyl)silyl]oxy}acetate (vi)
1-({[tert-butyl(diphenyl)silyl]oxy}methyl)cyclopropanol (vii)
diisopropyl bromomethylphosphonate (viii)
diisopropyl {[1-({[tert-butyl(diphenyl)silyl]oxy}methyl)cyclopropyl]oxy}methylphosphonate (ix)
diisopropyl {[1-(hydroxymethyl)cyclopropyl]oxy}methylphosphonate (x)
{1-[(diisopropoxyphosphoryl)methoxy]cyclopropyl}methyl methanesulfonate (xi)
4-chloro-1h-benzimidazol-6-amine; 4-chloro-1h-benzimidazol-6-ylamine (xiii)
Reference 1:
    chan, t.h.; li, l.; enantioselective synthesis of epigallocatechin-3-gallate (egcg), the active polyphenol component from green tea. org lett 2001, 3, 5, 739.

来源:药化网

作者:药化小编

摘要:本文合成路线介绍的是药物中文名(-)-表没食子儿茶素没食子酸酯;英文名(-)-Epigallocatechin gallate;(-)-EGCG;CAS[989-51-5]

 
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