178735-97-2

Upstream product

• 3978-80-1 Boc-Tyr-OH 
• 178357-86-3 (2R,5S)-2-(3-Fluoro-4-nitro-benzyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine 
• 131858-37-2 4-(bromomethyl)-2-fluoro-1-nitrobenzene 
• 113807-07-1 L-BOC-Tyr-OC₆F₅ 
• 178208-42-9 (R)-3-fluoro-4-nitrophenylalanine methyl ester 

Relevant academic research and scientific papers

Synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives

Full details of the synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives are detailed based on an intramolecular nucleophilic aromatic substitution reaction for formation of the key biaryl ether with 14-membered ring macrocyclization. Their comparison with prior samples and the documentation of a facile C9 epimerization within the natural 9S series are described.

Synthesis of (9S,12S)-cycloisodityrosine and its unnatural (9R,12S)- diastereomer

A synthesis of the (9S,12S)-cycloisodityrosine derivatives and their unnatural (9R,12S)-diastereomers are disclosed. The approach is based on an intramolecular aromatic nucleophilic substitution reaction for formation of the macrocyclic biaryl ether and includes the documentation of a remarkably facile base-catalyzed epimerization.