66154-72-1

Upstream product

• 108-24-7 acetic anhydride 
• 62562-76-9 benzyl 3-(2-hydroxyethyl)-4,5-dimethylpyrrole-2-carboxylate 
• 74839-03-5 5-ethoxycarbonyl-4-ethoxycarbonylmethyl-2-methylpyrrole-3-carboxylic acid 
• 62562-72-5 benzyl 3-(benzyloxycarbonylmethyl)-4,5-dimethylpyrrole-2-carboxylate 
• 54278-18-1 ethyl 3-(ethoxycarbonylmethyl)-4,5-dimethylpyrrole-2-carboxylate 
• 87377-63-7 ethyl 4-diethylaminomethyl-3-(ethoxycarbonylmethyl)-5-methylpyrrole-2-carboxylate 

Downstream Products

• 57907-69-4 benzyl-3-(2-acetoxyethyl)-5-acetoxymethyl-4-methylpyrrole-2-carboxylate 
• 75747-97-6 dibenzyl 4,4'-bis(2-acetoxyethyl)-3,3'-dimethylpyrromethane-5,5'-dicarboxylate 
• 87377-72-8 dibenzyl 3'-(2-chloroethyl)-4-(2-acetoxyethyl)-3,4'-dimethylpyrromethane-5,5'-dicarboxylate 
• 87377-71-7 C₃₁H₃₃ClN₂O₅ 
• 87377-64-8 5-benzyloxycarbonyl-4-(2-acetoxyethyl)-3-methylpyrrole-2-carboxylic acid 
• 87377-65-9 benzyl 5-iodo-3-(2-acetoxyethyl)-4-methylpyrrole-2-carboxylate 
• 87377-66-0 benzyl 3-(2-acetoxyethyl)-4-methylpyrrole-2-carboxylate 
• 104198-96-1 benzyl 3,3'-dimethyl-4-<β-(methoxycarbonyl)ethyl>-4'-(β-acetoxyethyl)-5'-<(tert-butyloxy)carbonyl>dipyrrylmethane-5-carboxylate 

Relevant academic research and scientific papers

Synthetic and Biosynthetic Studies of Porphyrins. Part 7. The Action of Coproporphyrinogen Oxidase on Coproporphyrinogen-IV: Syntheses of Protoporphyrin-XIII, Mesoporphyrin XIII, and Related Tricarboxylic Porphyrins

Coproporphyrinogen-IV (2a) is converted by an enzyme system from chicken blood into a tricarboxylic porphyrinogen (2b) and protoporphyrinogen-XIII (2c).The corresponding porphyrins were isolated as their methyl esters (3b) and (3c) and their structures were deduced by mass and n.m.r. spectrometry (including the use of shift reagents).Confirmation of these conclusions was obtained by total synthesis of the new porphyrins by the MacDonald and ac-biladiene routes.The vinyl groups were introduced either via acetoxyethyl side-chains derived from precursor pyrroles, or by reduction and dehydration of acetyl groups inserted into the porphyrins during the final stages of the syntheses.Mesoporphyrin-XIII dimethyl ester (3m) and the ethyl analogue (3n) of the vinyl tripropionate porphyrin (3b) were also synthesized by the MacDonald route.

Synthesis of a C-15-Substituted Porphyrin from a b-Bilene Precursor

The synthesis of a porphyrin substituted at C-13 with an ethoxycarbonyl residue and at C-15 with a β-(methoxycarbonyl)methyl side chain was attempted using a b-meso-substituted b-bilene-1',8'-di-tert-butyl ester precursor.The latter was obtained by conden

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).