79760-31-9

Upstream product

• 79760-30-8 Benzoic acid (5E,10Z,14Z,19Z)-13,18-bis-(2-hydroxy-ethyl)-3,7-bis-(2-methoxycarbonyl-ethyl)-2,8,12,17-tetramethyl-porphyrin-5-yl ester 
• 75630-46-5 benzyl 5-acetoxymethyl-3-(methoxycarbonylmethyl)-4-methylpyrrole-2-carboxylate 
• 98-88-4 benzoyl chloride 
• 87377-76-2 benzyl 4-ethoxycarbonylmethyl-3-methylpyrrole-2-carboxylate 
• 809-27-8 4,4'-bis-(2-methoxycarbonyl-ethyl)-3,3'-dimethyl-5,5'-methanediyl-bis-pyrrole-2-carboxylic acid 
• 87377-77-3 dibenzyl 3-ethoxycarbonylmethyl-4'-methoxycarbonylmethyl-4,3'-dimethylpyrromethane-5,5'-dicarboxylate 
• 87377-79-5 dibenzyl 3,4'-bis(2-acetoxyethyl)-4,3'-dimethylpyrromethane-5,5'-dicarboxylate 
• 87377-78-4 dibenzyl 3,4'-bis(2-hydroxyethyl)-4,3'-dimethylpyrromethane-5,5'-di-carboxylate 
• 79760-27-3 3,4'-bis(2-acetoxyethyl)-4,3'-dimethylpyrromethane-5,5'-dicarboxylic acid 
• 26019-74-9 5,5'-diformyl-4,4'-dimethyl-3,3'-bis-(methoxycarbonylethyl)-2,2'-dipyrryl ketone 
• 4792-10-3 3-{5-Formyl-2-[5-formyl-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrol-2-ylmethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acid methyl ester 
• 79760-29-5 2,4-bis(2-acetoxyethyl)-γ-benzoyloxy-6,7-bis(2-methoxycarbonylethyl)-1,3,5,8-tetramethylporphyrin 

Downstream Products

• 26280-00-2 biliverdin IX_γ dimethyl ester 

Relevant academic research and scientific papers

SYNTHESIS OF BILIVERDIN IXγ (PTEROBILIN)

Condensation of a bis(acetoxyethyl)pyrromethane dicarboxylic acid (11d) with a diformylpyrroketone (12b) afforded a bis(acetoxyethyl)-γ-meso-hydroxyporphyrin (13d) which was converted into the related bis(chloroethyl)-γ-benzoyloxyporphyrin (14f).The Zn complex of the latter was transformed by brief treatment with base, followed by chloromethylethyl ether into the zinc bis(chloroethyl)-γ-ethoxymethoxyporphyrin (20b).Dehydrochlorination with potassium t-butoxide in t-butanol, and acid catalysed demetallation and deprotection then afforded the somewhat unstable blue γ-oxyprotoporphyrin dimethyl ester (21).The Fe-complex of the latter readily underwent oxidative ring opening by aerial oxidation in pyridine, and after demetallation gave biliverdin IXγ (pterobilin) dimethyl ester (22).

Synthesis of γ-Oxyprotoporphyrin IX and Pterobiline (Biliverdin IXγ)

The γ-meso-hydroxy-derivative of protoporphyrin IX has been synthesised by condensation of a bis(formylpyrrolyl) ketone and a dipyrrolylmethane; the iron complex underwent oxidative ring-opening to give biliverdin IXγ (pterobiline), the blue-green butterfly pigment, thus providing a model for its biosynthesis.