133520-29-3

Upstream product

• 147-71-7 D-tartaric acid 
• 331-39-5 caffeic acid 
• 87-69-4 tartaric acid 
• 87-69-4 L-Tartaric acid 
• 6537-80-0 caftaric acid 
• 6537-80-0 (-)-chicoric acid 
• 204273-54-1 (2R,3R)-2,3-Bis-[(E)-3-(3,4-diacetoxy-phenyl)-acryloyloxy]-succinic acid di-tert-butyl ester 
• 82592-68-5 (E)-3,4-di-O-acetylcaffeoyl chloride 
• 203571-40-8 3-(3,4-bis-benzyloxy-phenyl)-acrylic acid ethyl ester 
• 54429-62-8 (E)-3-(3,4-bis(benzyloxy)phenyl)acrylic acid 
• 74257-25-3 ethyl caffeate 
• 488148-82-9 dibenzyl (-)-(2R,3R)-2,3-bis{3-[2,3-bis(3,4-dibenzyloxy)phenyl]prop-2-enoyloxy}-L-tartrate 
• 488148-83-0 dibenzyl (+)-(2S,3S)-2,3-bis{3-[3,4-bis(benzyloxy)phenyl]prop-2-enoyloxy}-D-tartrate 

Downstream Products

• 6537-80-0 cis-chicoric acid 

Relevant academic research and scientific papers

A convenient synthesis of the Echinacea-derived immunostimulator and HIV-1 integrase inhibitor (-)-(2R,3R)-chicoric acid

The Echinacea-derived immunostimulator and HIV-1 integrase inhibitor (-)-chicoric acid (=2,3-bis{[3- (3,4-dihydroxyphenyl)-1-oxoprop-2-enyl]oxy}butanedioic acid; 1a) was conveniently prepared via a silane-promoted Pd-mediated chemoselective hydrogenolysis of its perbenzylated derivative 12a, which was generated from an efficient and reliable carbodiimide-mediated coupling reaction between the caffeic acid dibenzyl ether derivative 7 and commercially available (+)-dibenzyl L-tartrate (9a). The other naturally occurring dextrorotatory chicoric acid (1b) can be similarly prepared.

Facile syntheses of (2R,3R)-(-)- and (2S,3S)-(+)-chicoric acids

Practical and efficient syntheses of (2R, 3R)-(-)- and (2S, 3S)(+)- chicoric acids are reported, which may be amenable to analogue preparation.