1452252-77-5

Upstream product

• 1443746-68-6 (R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanamido)-3-(((triisopropylsilyl)ethynyl)thio)propanoate 
• 1443746-72-2 (R)-ethyl 2-((S)-2-((1H-indol-3-yl)methyl)-3-(((benzyloxy)carbonyl)amino)-3-oxopropanamido)-3-mercaptopropanoate 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 

Downstream Products

• 1443746-73-3 (R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanamido)-3-((1-(3-(5-(dimethylamino)naphthalene-1-sulfonamido)propyl)-1H-1,2,3-triazol-4-yl)thio)propanoate 

Relevant academic research and scientific papers

A highly chemoselective and practical alkynylation of thiols

A thiol-alkynylation procedure utilizing the hypervalent iodine alkyne transfer reagent TIPS-ethynyl-benziodoxolone has been developed. This scalable reaction proceeds in five minutes at room temperature in an open flask using commercially available reagents. The scope of the reaction is broad, with a variety of phenolic, benzylic, heterocyclic, and aliphatic thiols undergoing alkynylation in excellent yield. The method is highly chemoselective as a vast array of functional groups are tolerated. The utility of the thiol-alkynylation in postsynthetic elaboration has been demonstrated through the facile installment of a fluorophore tag on a cysteine-containing peptide.