208586-06-5

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 208585-91-5 (S)-2-[(2S,3R)-3-tert-Butoxycarbonylamino-2-hydroxy-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 208585-83-5 2-((1S,7aR)-5,5-Dimethyl-3-oxo-dihydro-thiazolo[3,4-c]oxazol-1-yl)-2-methyl-propionic acid 
• 208585-87-9 (S)-2-[1-((4R,5S)-4-Mercaptomethyl-2-oxo-oxazolidin-5-yl)-1-methyl-ethyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester 
• 208585-79-9 (R)-4-(2-Methoxycarbonyl-2-methyl-propionyl)-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 208585-85-7 (S)-2-[2-((1S,7aR)-5,5-Dimethyl-3-oxo-dihydro-thiazolo[3,4-c]oxazol-1-yl)-2-methyl-propionylamino]-3-mercapto-2-methyl-propionic acid methyl ester 
• 208585-89-1 (S)-2-{1-[(4R,5S)-4-(4-Methoxy-benzylsulfanylmethyl)-2-oxo-oxazolidin-5-yl]-1-methyl-ethyl}-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester 
• 208585-81-3 (R)-4-((S)-1-Hydroxy-2-methoxycarbonyl-2-methyl-propyl)-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 249271-64-5 2-((1S,7aR)-5,5-Dimethyl-3-oxo-dihydro-thiazolo[3,4-c]oxazol-1-yl)-2-methyl-propionic acid methyl ester 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 249271-59-8 (S)-2-[(2S,3R)-3-(tert-Butoxycarbonyl-methyl-amino)-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester 
• 208585-91-5 (S)-2-[(2S,3R)-3-tert-Butoxycarbonylamino-2-hydroxy-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester 
• 208585-93-7 (S)-2-[(2S,3R)-3-(tert-Butoxycarbonyl-methyl-amino)-2-hydroxy-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester 
• 287967-62-8 (S)-2-[(2S,3R)-3-(tert-Butoxycarbonyl-methyl-amino)-2-hydroxy-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid 

Relevant academic research and scientific papers

Synthetic studies of thiazoline and thiazolidine-containing natural products - 2. Total synthesis of the antimycoplasma antibiotic micacocidin

Synthesis of the fight half of micacocodin (segment B) and subsequent completion of total synthesis of the antimycoplasma antibiotic micacocidin is described. The desired S-configuration at C-14 secondary carbinol was obtained by stereoselective reduction of the preceding ketone in accordance with the Cram rule. Condensation of two labile segments, A and B, was achieved in the presence of potassium acetate. The chiral center at C-10 was finally isomerized to the natural configuration through formation of the Zn complex.

Total synthesis of the antimycoplasma antibiotic micacocidin

A total synthesis of the antimycoplasma antibiotic micacocidin (1) is described. Construction of sterically hindered thiazoline 12 was achieved by a phosphorus pentachloride-mediated cyclization reaction of S-protected aryloylcysteine 11, and compound 1 with desired chirality at C-10 was favorably obtain from diastereomeric mixture 30 through formation of the Zn complex 31.