56776-34-2

Upstream product

• 122902-81-2 N-Boc-N-methyl-L-serine methyl ester 

Downstream Products

• 601507-06-6 (2-amino-1-benzyl-4-oxo-1,4,5,6-tetrahydro-pyrimidin-5-yl)-methyl-carbamic acid tert-butyl ester 
• 130291-54-2 2-(tert-Butoxycarbonyl-methyl-amino)-3-[(4aR,8aR)-1,6-dioxo-2-(toluene-4-sulfonyl)-2,3,4,4a,5,6-hexahydro-1H-isoquinolin-8a-yl]-propionic acid methyl ester 
• 130291-51-9 3-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-5,6-dihydro-2(1H)-pyridinone 
• 601507-18-0 C₂₆H₃₁N₅O₆ 
• 601507-14-6 C₂₀H₂₇N₅O₆ 
• 601507-16-8 [2-(acetyl-methyl-amino)-1-benzyl-4-oxo-1,4,5,6-tetrahydro-pyrimidin-5-yl]-methyl-carbamic acid tert-butyl ester 
• 554412-66-7 5-(tert-butoxycarbonyl-methyl-amino)-2-methylsulfanyl-4-oxo-5,6-dihydro-4H-pyrimidine-1-carboxylic acid benzyl ester 
• 601507-08-8 (1-benzyl-2-imino-3-methyl-4-oxo-hexahydro-pyrimidin-5-yl)-methyl-carbamic acid tert-butyl ester 
• 601507-10-2 (1-benzyl-2-methylamino-4-oxo-1,4,5,6-tetrahydro-pyrimidin-5-yl)-methyl-carbamic acid tert-butyl ester 
• 130291-49-5 2-(tert-Butoxycarbonyl-methyl-amino)-3-[2-oxo-3-phenylsulfanyl-1-(toluene-4-sulfonyl)-piperidin-3-yl]-propionic acid methyl ester 

Relevant academic research and scientific papers

Total Synthesis of TAN-1057 A/B, a New Dipeptide Antibiotic from Flexibacter sp. PK-74

TAN-1057 (1a, b) - a new natural dipeptide antibiotic active against methicillin resistant strains of Staphylococcus aureus - was synthesized starting from Na,Nδ,Nω-tri-Z-L-arginine 20b via the corresponding diazoketone 21b. This upon photolysis rearranged to the ketene which was trapped by (±)-2,4,5,6-tetrahydro-5-methylamino-2-ureidopyrimidin-4-one (3) to yield the fully protected dipeptide 23 (30%). The latter was deprotected by hydrogenolysis to give the final compound as a mixture of two epimers - TAN-1057A, B - isolated previously from a strain of Flexibacter sp. PK-74. The intermediate 3 was prepared from 3-amino-2-(N-Z-N-methylamino)propionic acid methyl ester hydrochloride (16) and 2-methyl-2-thiopseudobiuret hydroiodide (18) in one step in 35% yield.