155104-38-4

Upstream product

• 15960-81-3 benzyl bromomethyl thioether 
• 1142-20-7 N-Cbz-Ala 
• 171860-41-6 (S,S)-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 

Downstream Products

• 177546-83-7 ((S)-2-Benzylsulfanyl-1-{(R)-2-benzylsulfanyl-1-[(R)-2-benzylsulfanyl-1-(2-benzylsulfanyl-ethylcarbamoyl)-1-methyl-ethylcarbamoyl]-1-methyl-ethylcarbamoyl}-1-methyl-ethyl)-carbamic acid benzyl ester 
• 155104-39-5 (R)-2-[(R)-2-((S)-2-Benzyloxycarbonylamino-3-benzylsulfanyl-2-methyl-propionylamino)-3-benzylsulfanyl-2-methyl-propionylamino]-3-benzylsulfanyl-2-methyl-propionic acid methyl ester 
• 191734-57-3 {(S)-2-Benzylsulfanyl-1-[(R)-2-benzylsulfanyl-1-((R)-2-benzylsulfanyl-1-carbamoyl-1-methyl-ethylcarbamoyl)-1-methyl-ethylcarbamoyl]-1-methyl-ethyl}-carbamic acid benzyl ester 
• 155104-40-8 N-(2-methylpropionyl)-S-benzyl-(S)-2-methylcysteinyl-S-benzyl-(R)-methylcysteinyl-S-benzyl-(R)-methylcysteine N-((benzylthio)ethyl)amide 
• 154960-17-5 (R)-3-Benzylsulfanyl-2-[(R)-3-benzylsulfanyl-2-((S)-3-benzylsulfanyl-2-isobutyrylamino-2-methyl-propionylamino)-2-methyl-propionylamino]-2-methyl-propionic acid methyl ester 
• 154960-18-6 (R)-3-Benzylsulfanyl-2-[(R)-3-benzylsulfanyl-2-((S)-3-benzylsulfanyl-2-isobutyrylamino-2-methyl-propionylamino)-2-methyl-propionylamino]-2-methyl-propionamide 

Relevant academic research and scientific papers

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

(-)-Mirabazole B (1), an alkaloid consisting of four successive thiazoline/thiazole rings, has been synthesized in a convergent route. The key intermediate, a linear tripeptide amide 13 composing of three S-benzyl-2-methylcysteine residues, was prepared u

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.