765299-27-2

Upstream product

• 60079-12-1 β-Methyl α-tert-butyl (2S)-N-(benzyloxycarbonyl)aspartate 
• 74-88-4 methyl iodide 

Downstream Products

• 765299-33-0 C₂₀H₂₉N₅O₆S 
• 765299-29-4 (S)-3-tert-butoxycarbonyl-3-[(N-benzyloxycarbonyl-N-methyl)amino]propanoylsuccinimide 
• 765299-32-9 (S)-2-(N-benzyloxycarbonyl-N-methyl)amino-3-(tert-butoxycarbonylamino)propionic acid 
• 765299-30-7 N²-benzyloxycarbonyl-N²-methyl-L-asparagine tert-butyl ester 
• 475296-58-3 N²-benzyloxycarbonyl-N²-methyl-L-asparagine 
• 147634-99-9 (2S)-N²-carbobenzoxy-N²-methyl-2,3-diaminopropionic acid 
• 765299-28-3 1-tert-butyl (S)-N-benzyloxycarbonyl-N-methylaspartate 

Relevant academic research and scientific papers

First enantioselective synthesis of the novel antiinfective TAN-1057A via its aminomethyl-substituted dihydropyrimidinone heterocycle

Enantiomerically pure N2-Z-N2-MeAsnOH [(S)-14], prepared in 8 steps (23% overall yield) from asparaginic acid, was first subjected to a Hofmann degradation with PhI(OCOCF3)2 yielding (S)-N2-Z-N2-methyl-2,3-diaminopropanoic acid [N2-Z-N2-Me-L-A2pr, (S)-15], and this in turn was protected to give N2-Z-N3-Boc-N2-Me-L- A2pr [(S)-17]. Condensation of (S)-17 with HNC(SMe)NHCONH2 followed by removal of the tert-butoxycarbonyl protecting group, cyclization and hydrogenolytic removal of the Z-group gave the heterocycle of TAN-1057A [(S)-1] with an e.e. of 87 in 36% yield [from (S)-14]. Coupling of (S)-1 with (S)-tris-Z-β-homoarginine (20a) in the presence of O-(7-azabenzotriazol-1- yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) and iPr2NEt in N,N-dimethylacetamide followed by hydrogenolysis afforded the most active A-diastereomer of the natural antibiotic TAN-1057 in 52% yield (from (S)-1 and 20a). Similarly, starting from (S)-1, a single diastereomer of the potent, less toxic TAN-1057A analogue 22b with a β-lysine side chain has been prepared. All described synthetic steps do not require column chromatography for purification of the products.