143564-91-4

Upstream product

• 143564-90-3 (2R,4R)-4-Benzylsulfanylmethyl-4-methyl-5-oxo-2-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 15960-81-3 benzyl bromomethyl thioether 
• 26607-51-2 N-benzyloxycarbonyl-D-alanine 
• 135923-86-3 (2R,4R)-3-<(Benzyloxy)carbonyl>-4-methyl-2-phenyl-1,3-oxazolidin-5-one 

Downstream Products

• 143564-94-7 (R)-2-((R)-2-Benzyloxycarbonylamino-3-benzylsulfanyl-2-methyl-propionylamino)-3-benzylsulfanyl-2-methyl-propionic acid methyl ester 
• 191734-53-9 [(R)-2-Benzylsulfanyl-1-((R)-2-benzylsulfanyl-1-carbamoyl-1-methyl-ethylcarbamoyl)-1-methyl-ethyl]-carbamic acid benzyl ester 
• 249749-42-6 (R)-S-benzyl-α-methylcysteine 
• 143565-00-8 (R)-3-Benzylsulfanyl-N-[(R)-2-benzylsulfanyl-1-(2-benzylsulfanyl-ethylcarbamoyl)-1-methyl-ethyl]-2-((R)-3-benzylsulfanyl-2-isobutyrylamino-2-methyl-propionylamino)-2-methyl-propionamide 
• 143564-98-1 (R)-3-Benzylsulfanyl-2-[(R)-3-benzylsulfanyl-2-((R)-3-benzylsulfanyl-2-isobutyrylamino-2-methyl-propionylamino)-2-methyl-propionylamino]-2-methyl-propionic acid methyl ester 
• 143564-99-2 (R)-3-Benzylsulfanyl-2-[(R)-3-benzylsulfanyl-2-((R)-3-benzylsulfanyl-2-isobutyrylamino-2-methyl-propionylamino)-2-methyl-propionylamino]-2-methyl-propionic acid 
• 158395-12-1 (R)-2-[(R)-2-((R)-2-Amino-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 
• 155104-39-5 (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 
• 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 
• 745761-96-0 (R)-2-((R)-2-Amino-3-benzylsulfanyl-2-methyl-propionylamino)-3-benzylsulfanyl-2-methyl-propionic acid methyl ester 
• 249749-37-9 Boc-(R)-MeCys(Bn)-(R)-MeCys(Bn)-(R)-MeCys(Bn)-Thr(Bn)-NHCH₃ 
• 249749-35-7 Boc-(R)-MeCys(Bn)-(R)-MeCys(Bn)-Thr(Bn)-NHCH₃ 

Relevant academic research and scientific papers

Total synthesis of thiangazole

A method for total synthesis of thiangazole (1), a tris-thiazoline- oxazole metabolite, is described. The key intermediate 9, a linear tetrapeptide amide composed of three S-benzyl-2-methylcysteine residues and a O-benzyl-threonine amide, was synthesized in 4 steps using 2-chloro-1,3- dimethyl-imidazolidium hexafluorophosphate(CIP)mediated activation. The successive thiazoline/oxazole rings were constructed by TiCl4mediated cycledehydration followed by acid-catalyzed Robinson-Gabriel reaction without difficulty.

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.