37945-74-7

Upstream product

• 546-67-8 lead(IV) tetraacetate 
• 51089-69-1 benzyl 4-(2'-chloroethyl)-3,5-dimethylpyrrole-2-carboxylate 
• 31837-63-5 benzyl 4-(2-hydroxyethyl)-3,5-dimethylpyrrole-2-carboxylate 
• 64-19-7 acetic acid 

Downstream Products

• 37945-76-9 4-(2-chloro-ethyl)-3-methyl-5-(3-methyl-7-oxo-1,4,5,7-tetrahydro-pyrano[3,4-b]pyrrol-2-ylmethyl)-pyrrole-2-carboxylic acid benzyl ester 
• 51089-81-7 4-(2-chloro-ethyl)-5-(7-dimethylamino-3-methyl-4,5-dihydro-pyrano[3,4-b]pyrrol-2-ylmethyl)-3-methyl-pyrrole-2-carboxylic acid benzyl ester; protonated form 
• 75488-04-9 benzyl 5'-(t-butyloxycarbonyl)-3-(2-chloroethyl)-4'-ethyl-3',4-dimethyldipyrrylmethane-5-carboxylate 
• 135363-71-2 Benzyl 5'-tert-Butoxycarbonyl-3,4'-bis(2-chloroethyl)-1',3',4-trimethyldipyrromethane-5-carboxylate 
• 87377-71-7 C₃₁H₃₃ClN₂O₅ 
• 127798-84-9 tert-butyl-3,4'-dimethyl-4-<β-(ethoxycarbonyl)ethyl>-3'-<β-chloroethyl>-5'-<(benzyloxy)carbonyl>dipyrrylmethane-5-carboxylate 
• 97346-02-6 C₂₈H₃₅ClN₂O₄ 
• 63089-18-9 dibenzyl 3,3'-bis-(2-chloroethyl)-4,4'-dimethylpyrromethane-5,5'-dicarboxylate 
• 162661-60-1 1-benzyloxycarbonyl-3-(2-chloroethyl)-2,8-dimethyl-7-(2-ethoxycarbonylethyl)-9-tert-butyloxycarbonyldipyrrylmethane 
• 51089-85-1 tert-butyl 5'-(benzyloxycarbonyl)-3'-(2-chloroethyl)-4-(2-methoxycarbonylethyl)-3,4'-dimethyl-2,2'-dipyrrylmethane-5-carboxylate 
• 87377-72-8 dibenzyl 3'-(2-chloroethyl)-4-(2-acetoxyethyl)-3,4'-dimethylpyrromethane-5,5'-dicarboxylate 
• 54605-90-2 tert-butyl 5'-<(benzyloxy)carbonyl>-3',4-bis(2-chloroethyl)-3,4'-dimethyldipyrrylmethane-5-carboxylate 
• 87944-89-6 dibenzyl 3-(2-chloroethyl)-3',4,4'-trimethylpyrromethane-5,5'-dicarboxylate 

Relevant academic research and scientific papers

Syntheses of protoporphyrin-IX derivatives bearing extended propionate side-chains

In order to investigate the relationship between depth within membranes of singlet oxygen generation and effectiveness of photodynamic therapy of tumors, analogs of protoporphyrin-IX 1 bearing five 4 and seven 5 carbon atoms (in place of the 3-carbon atom

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).