117625-52-2

Upstream product

• 110828-48-3 Benzoic acid (3aR,4R,5R,6aS)-4-{(E)-5-[2-(tert-butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-oxo-pent-1-enyl}-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 39746-01-5 (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one 
• 110828-45-0 {4-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-2-oxo-butyl}-phosphonic acid dimethyl ester 
• 117625-50-0 3-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-propionic acid methyl ester 
• 103515-26-0 7-trifluoroacetamido-3,4-dihydrocoumarin 
• 103489-31-2 β-(4-azidophenyl)-propanoic acid 
• 110828-47-2 3-(4-Amino-2-hydroxy-phenyl)-propionic acid methyl ester 
• 76-83-5 trityl chloride 
• 117625-51-1 Benzoic acid (3aR,4R,5R,6aS)-4-{(E)-(S)-5-[2-(tert-butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-hydroxy-pent-1-enyl}-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 110828-48-3 Benzoic acid (3aR,5R,6aS)-4-{(E)-5-[2-(tert-butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-oxo-pent-1-enyl}-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 117625-49-7 3-[2-Hydroxy-4-(trityl-amino)-phenyl]-propionic acid methyl ester 
• 2393-17-1 3-(4-aminophenyl)propionic acid 
• 882-06-4 4-nitro-trans-cinnamic acid 
• 39746-01-5 Benzoic acid (3aR,5R,6aS)-4-formyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 

Downstream Products

• 117625-53-3 (3aR,5R,6aS)-4-[(E)-(S)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one 
• 117625-53-3 (3aR,4R,5R,6aS)-4-[(E)-(S)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one 
• 117625-54-4 (Z)-7-[(1R,2R,3R,5S)-2-[(E)-(S)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid 
• 110828-49-4 (3aR,4R,5R,6aS)-4-[(E)-(S)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol 
• 110828-44-9 (Z)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-2-hydroxy-phenyl)-3-hydroxy-pent-1-enyl]-3,5-dihydroxy-cyclopentyl}-hept-5-enoic acid 
• 117625-54-4 (Z)-7-[(1R,3R,5S)-2-[(E)-(S)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid 
• 110828-50-7 (Z)-7-[(1R,3R,5S)-5-Hydroxy-2-[(E)-(S)-5-[2-hydroxy-4-(trityl-amino)-phenyl]-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid 
• 110828-49-4 (3aR,5R,6aS)-4-[(E)-(S)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol 

Relevant academic research and scientific papers

Prostaglandin Photoaffinity Probes: Synthesis and Biological Activity of Azide-Substituted 16-Phenoxy- and 17-Phenyl-PGF2α Prostaglandins

The development of a prostaglandin PGF2α photoaffinity probe led to the synthesis and biological evaluation of azide-substituted 17-phenyl-18,19,20-trinorprostaglandin F2α and 16-phenoxy-17,18,19,20-tetranorprostaglandin F2α derivatives.Two approaches for the preparation of iodinated versions of these prostaglandins were evaluated: (1) iodination of a phenyl azide bearing an activating hydroxyl group and (2) iodination of an aniline precursor to the phenyl azide group and subsequent conversion of the aniline to the phenyl azide.In the first approach, 17-(4-azido-2-hydroxyphenyl)-18,19,20-trinorprostaglandin F2α, 16-(5-azido-3-hydroxyphenoxy)-17,18,19,20-tetranorprostaglandin F2α, and 16-(4-azido-2-hydroxyphenoxy)-17,18,19,20-tetranorprostaglandin F2α were prepared by using the Corey synthesis, but were biologically inactive presumably as a result of the hydrophilic phenolic hydroxyl group.In the second approach, the iodination of a 17-(4-aminophenyl)-18,19,20-trinorprostaglandin F2α derivative delivered 17-(4-azido-3-iodophenyl)-18,19,20-trinorprostaglandin F2α, which exhibited competitive binding with natural PGF2α to ovine luteal cells and to plasma membranes of bovine corpora lutea. -17-(4-Azido-3-iodophenyl)-18,19,20-trinorprostaglandin F2α was utilized in a preliminary photoaffinity cross-linking experiment.

UTILIZATION OF A NITRENIUM ION CYCLIZATION IN A SYNTHESIS OF A PHOTOACTIVE PROSTAGLANDIN, 17-(4-AZIDO-2-HYDROXYPHENYL)-18,19,20-TRINORPROSTAGLANDIN F2α

A nitrenium ion cyclization provided access to a suitably substituted arylpropionic ester needed in the synthesis of a potential prostaglandin photoaffinity probe, 17-(4-azido-2-hydroxyphenyl)-18,19,20-trinorprostaglandin F2α using the Corey synthesis.