348128-89-2

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 156459-19-7 3-cyano-6-(dimethoxymethyl)-2-pyridone 
• 156459-20-0 6-(dimethoxymethyl)-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid 
• 348128-80-3 2-(1-tert-butoxycarbonylamino-ethyl)-6-{4-[1-tert-butoxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-ethylthiocarbamoyl]-thiazol-2-yl}-nicotinic acid benzyl ester 
• 348128-79-0 2-(1-tert-butoxycarbonylamino-ethyl)-6-{4-[1-tert-butoxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-thiazol-2-yl}-nicotinic acid benzyl ester 
• 348128-73-4 phenacyl (RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylate 
• 348128-78-9 2-(1-tert-butoxycarbonylamino-ethyl)-6-{4-[1-tert-butoxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-thiazol-2-yl}-nicotinic acid 
• 348128-81-4 2-(1-tert-butoxycarbonylamino-ethyl)-6-[4-(1-tert-butoxycarbonyl-2-hydroxy-ethylthiocarbamoyl)-thiazol-2-yl]-nicotinic acid benzyl ester 
• 348128-77-8 2-{4-[1-tert-butoxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-thiazol-2-yl}-7-methyl-5-oxo-5,7-dihydro-pyrrolo[3,4-b]pyridine-6-carboxylic acid tert-butyl ester 
• 348128-83-6 t-butyl (4S)-2-(2-{3-benzyloxycarbonyl-2-[(1R)-1-t-butoxycarbonylaminoethyl]pyridin-6-yl}-1,3-thiazol-4-yl)-4,5-dihydro-1,3-thiazole-4-carboxylate 
• 348128-72-3 (RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylic acid 
• 348128-71-2 methyl (RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylate 
• 348128-74-5 phenacyl (RS)-2-[2-(1-t-butoxycarbonylaminoethyl)-3-(hydroxymethyl)pyridin-6-yl]-1,3-thiazole-4-carboxylate 
• 348128-69-8 (RS)-2-(1-t-butoxycarbonylaminoethyl)-3-(t-butyldiphenylsiloxymethyl)-6-(dimethoxymethyl)pyridine 

Relevant academic research and scientific papers

Novel synthesis of the main central 2,3,6-trisubstituted pyridine skeleton [Fragment A-B-C] of a macrobicyclic antibiotic, cyclothiazomycin

The useful synthesis of the main central 2,3,6-trisubstituted pyridine skeleton [the protected Fragment A-B-C] of a macrobicyclic antibiotic, cyclothiazomycin, was first accomplished. First, the 2-[2-(2-substituted thiazol-4-yl)]-4,5-dihydrothiazole-4-carboxylate [Fragment A derivative], attached to the 6-substituent of the main pyridine skeleton, was synthesized by two consecutive thiazolations of the protected Ser thioamide derivative with 3-bromopyruvate, and then thiazolination of the C-terminal Ser residue of the sequence. Secondly, an efficient synthesis of the central 2-(2-{2[(1R)-1-aminoethyl]pyridin-6-yl}thiazol-4-yl)-4, 5-dihydrothiazole-4-carboxylate [Fragment B derivative] was also achieved by thiazolation of the formyl group of the 2-(1-aminoethyl)-6-formylpyridine derivative, and then thiazolination. Thirdly, a convenient synthesis of the protected dehydrotetrapeptide [Fragment C derivative], which is bound to the 2-substituent of the pyridine skeleton, was attained by the usual stepwise elongation of the appropriate α-amino acids and β-elimination of a Thr residue of the sequence. Finally, the facile fragment condensation of the three Fragments thus obtained gave the protected Fragment A-B-C derivative via Fragment A-B. Furthermore, the configurational structures of the three Fragments (A, B, and C) were also investigated.

Convenient synthesis of a central 2,3,6-trisubstituted pyridine skeleton of a macrobicyclic antibiotic, cyclothiazomycin

The first convenient synthesis of the main central 2,3,6-trisubstituted pyridine skeleton [protected Fragment A-B] of a macrobicyclic antibiotic, cyclothiazomycin, was achieved.