177546-83-7

Upstream product

• 15960-81-3 benzyl bromomethyl thioether 
• 143564-90-3 (2R,4R)-4-Benzylsulfanylmethyl-4-methyl-5-oxo-2-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 177696-13-8 (2S,4S)-4-Benzylsulfanylmethyl-4-methyl-5-oxo-2-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 177546-82-6 {(R)-2-Benzylsulfanyl-1-[(R)-2-benzylsulfanyl-1-(2-benzylsulfanyl-ethylcarbamoyl)-1-methyl-ethylcarbamoyl]-1-methyl-ethyl}-carbamic acid benzyl ester 
• 155104-38-4 N^α-benzyloxycarbonyl-S-benzyl-(S)-methylcysteine 
• 177546-81-5 [(R)-2-Benzylsulfanyl-1-(2-benzylsulfanyl-ethylcarbamoyl)-1-methyl-ethyl]-carbamic acid benzyl ester 
• 143564-91-4 N^α-benzyloxycarbonyl-S-benzyl-(R)-methylcysteine 
• 171860-41-6 (S,S)-4-methyl-5-oxo-2-phenyl-oxazolidine-3-carboxylic acid benzyl ester 

Downstream Products

• 155104-40-8 N-(2-methylpropionyl)-S-benzyl-(S)-2-methylcysteinyl-S-benzyl-(R)-methylcysteinyl-S-benzyl-(R)-methylcysteine N-((benzylthio)ethyl)amide 

Relevant academic research and scientific papers

Convergent synthesis of (-)-mirabazole C using a chloroimidazolidium coupling reagent, CIP

Convergent synthesis of (-)-mirabazole C (1), a tetra thiazoline/thiazole alkaloid isolated from blue-green alga, has been described. The successive thiazoline rings of (-)-mirabazole C were formed by a single-step cyclization mediated by TiCl4 treatment of tripeptide amide 4. Convergent synthesis of the key intermediate 33 derived from three 2-methylcysteine residues was first achieved using a newly developed coupling reagent, 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate (CIP). The effectiveness of CIP for the coupling of α,α-dialkyl amino acids and the reaction pathway of the activation were clarified by the syntheses of model peptides containing an α,α-dimethylamino acid. A practical method of asymmetric synthesis of 2-methylcysteine by alkylation of 2,4-cis-oxazolidinone 23 has also been described.