87377-70-6

Upstream product

• 546-67-8 lead(IV) tetraacetate 
• 31837-62-4 benzyl 4-<(methoxycarbonyl)methyl>-3,5-dimethylpyrrole-2-carboxylate 

Downstream Products

• 154435-79-7 2,5-bis(<5-benzyloxycarbonyl-3-(methoxycarbonylmethyl)-4-methyl-1H-pyrrol-2-yl>methyl)-3,4-dimethylpyrrole 
• 87377-74-0 benzyl 3-(methoxycarbonylmethyl)-4'-(ethoxycarbonylmethyl)-3',4-dimethyl-5'-ethoxycarbonylpyrromethane-5-carboxylate 
• 111782-62-8 C₃₃H₃₄N₂O₈ 
• 97346-04-8 C₃₃H₃₄N₂O₈ 
• 97345-99-8 C₃₁H₃₈N₂O₈ 
• 97346-00-4 C₂₉H₃₆N₂O₆ 
• 87377-75-1 benzyl 3,4'-bis-(2-hydroxyethyl)-3',4-dimethyl-5'-ethoxycarbonylpyrromethane-5-carboxylate 

Relevant academic research and scientific papers

Synthetic and Biosynthetic Studies of Porphyrins.Part10.Syntheses of Porphyrins with Acetic,Propionic,and Butyric Acid Side-chains for Biosynthetic Syudies.

In connection with studies of substrate specificity of uroporphyrinogen decarboxylase and coproporphyrinogen oxidase, enzymes in the heme and chlorophyll biosynthetic pathways,and heme oxygenase,an enzyme involved in the catabolism of hemes,we have synthesized a number of new porphyrins substituted with acetic,propionic,and butyric side-chains,using the a,c-biladiene route;one porphyrin was also prepared by the MacDonald pyrromethane approach.In one of the a,c-biladiene cyclizations,meso-chlorinated porphyrins were formed as minor by products,but this side-reaction was suppressed by carefully drying the copper(II) chloride used in this stage, or by use of copper(II) acetate as an alternative oxidant.

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).