376586-85-5

Upstream product

• 96551-21-2 1-(t-butyloxycarbonyl)-3-(bromomethyl)indole 
• 376586-88-8 3-benzyloxycarbonyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 98-79-3 L-Pyroglutamic acid 
• 4931-66-2 methyl (S)-pyroglutamate 
• 17342-08-4 (S)-Pyroglutaminol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 106191-02-0 (S)-5-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-2-one 
• 81658-26-6 tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate 

Relevant academic research and scientific papers

Diastereoselective formation of a quaternary center in a pyroglutamate derivative. Formal synthesis of Monatin

In this communication we describe a highly diastereoselective formation of a quaternary center present in the structure of Monatin, a potent sweetening agent isolated from natural sources. The synthesis of a derivative useful for biological studies on the interactions of this type of sweetening substance on taste receptors is described. The strategy relies on the oxidation of an enolate originating from a pyroglutamate derivative followed by a highly diastereoselective alkylation with an electrophile obtained from indole.