205492-41-7

Upstream product

• 184775-08-4 benzyl 4-(1-hydroxy-2,2,2-trifluoroethyl)-3,5-dimethylpyrrole-2-carboxylate 
• 40236-19-9 benzyl 3,5-dimethylpyrrole-2-carboxylate 
• 205492-38-2 benzyl 3,5-dimethyl-4-(trifluoroacetyl)pyrrole-2-carboxylate 

Downstream Products

• 220802-59-5 benzyl 4-methyl-3-((R)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate 
• 220802-51-7 benzyl 4-((R)-1-acetoxy-2,2,2-trifluoroethyl)-5-methoxycarbonyl-3-methylpyrrole-2-carboxylate 
• 220802-49-3 3-(1-acetoxy-2,2,2-trifluoro-ethyl)-4-methyl-1H-pyrrole-2,5-dicarboxylic acid 5-benzyl ester 
• 220802-69-7 dibenzyl (3S,4'R)-4,3'-dimethyl-3,4'-bis(2,2,2-trifluoro-1-hydroxyethyl)-2,2'-dipyrrylmethane-5,5'-dicarboxylate 
• 220802-66-4 dibenzyl (3R,4'S)-4,3'-dimethyl-3,4'-bis(2,2,2-trifluoro-1-hydroxyethyl)-2,2'-dipyrrylmethane-5,5'-dicarboxylate 
• 380231-94-7 benzyl 5-acetoxymethyl-3-methyl-4-((R)-2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate 

Relevant academic research and scientific papers

Syntheses of chiral fluorine analogs of hematoporphyrin

Four chiral fluorine analogs of hematoporphyrin, (R,R)-, (R,S)-, (S,R)-, and (S,S)-3,8-bis(2,2,2-trifluoro-1-hydroxyethyl)deuteroporphyrins, were synthesized starting from pyrroles with a chiral 2,2,2-trifluoro-1-hydroxyethyl (TFHE) group. This chiral TFHE group was obtained by asymmetric reduction of a trifluoroacetyl group. Among these chiral analogs of hematoporphyrin, the (S,S)-isomer showed higher affinity for cancer cells than other stereoisomers.

Optical resolution and asymmetric synthesis of benzyl 3,5-dimethyl-4-(2,2,2-trifluoro-1-hydroxyethyl)-pyrrole-2-carboxylate

For the total synthesis of 3- and 8-(2,2,2-trifluoro-1-hydroxyethyl)-deuteroporphyrin dimethyl esters (2, and 3) in a large scale by ring closure, the camphanyl ester (5) of the titled ester (4) was resolved, but hydrolysis of the resolved 5 was unsuccess