181772-74-7

Upstream product

• 181772-66-7 3''-pentyl (R,E)-4-[2,2-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]but-2-enoate 
• 181772-61-2 (R)-2-[2',2'-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]ethanal 
• 38235-77-7 (R)-N-benzyl-1-phenylethylamine 
• 59956-49-9 bromoacetic acid,3-pentyl ester 
• 584-02-1 2-pentanol 
• 1262515-99-0 [2-oxo-2-(3'-pentyloxy)ethyl]triphenylphosphonium bromide 
• 181772-56-5 ethyl (R)-[2',2'-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]ethanoate 
• 181772-82-7 (R)-2-[2',2'-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]ethanol 
• 181772-51-0 ethyl (3R)-4-(tert-butyloxycarbonyl)amino-3-hydroxybutanoate 

Downstream Products

• 181772-92-9 (R)-5-{(R)-2-[Benzyl-((R)-1-phenyl-ethyl)-amino]-3-carboxy-propyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 33404-78-3 negamycin 
• 181772-78-1 benzyl (R,R,R)-N(1')-methyl-N(2')-(3'-[N-benzyl-N-(α-methylbenzyl)amino]-4''-[2''',2'''-dimethyl-N(3''')-tert-butoxycarbonyl-1''',3'''-oxazolidin-5'''-yl]butanoyl)hydrazinylethanoate 
• 1262515-94-5 3'-pentyl (R,R)-3-(N-benzyloxycarbonylamino)-4-[N(3')-tert-butoxycarbonyl-2',2'-dimethyl-1',3-oxazolidin-5'-yl]butanoate 
• 1262515-95-6 C₁₅H₂₂N₂O₅*ClH 
• 141734-42-1 methyl (R,R,E,E)-3-(N-benzyloxycarbonylamino)-5-hydroxy-6-[N-(2',4'-hexadienoyl)amino]hexanoate 
• 1262515-96-7 methyl (R,R,E,E)-3-(N-benzyloxycarbonylamino)-4-[2',2'-dimethyl-N(3')-(2,4-hexadienoyl)-1',3'-oxazolidin-5'-yl]butanoate 
• 1262515-97-8 (R,R,E,E)-3-(n-benzyloxycarbonylamino)-4-[N(3')-(2'',4''-hexadienoyl)-2',2'-dimethyl-1',3'-oxazolidin-5'-yl]butanoic acid 
• 111337-86-1 2'-amidinoethyl (R,R,E,E)-3-amino-5-hydroxy-6-[N-(2'',4''-hexadienoyl)amino]butanamide 

Relevant academic research and scientific papers

Asymmetric syntheses of (+)-negamycin, (+)-3-epi-negamycin and sperabillin C via lithium amide conjugate addition

The chemo- and enantioselective reduction of ethyl 4-chloroacetoacetate and the diastereoselective conjugate addition of enantiopure lithium N-benzyl-N-(α-methylbenzyl)amide to an α,β-unsaturated ester have been used as the key steps in the total asymmetric syntheses of (+)-negamycin (in 13 steps and 24% overall yield), (+)-3-epi-negamycin (in 13 steps and 10% overall yield) and sperabillin C (in 17 steps and 13% overall yield) from commercially available starting materials.

Asymmetric synthesis of (+)-negamycin

(+)-Negamycin was synthesised employing the highly diastereoselective conjugate addition of lithium (α-methylbenzyl)benzylamide in the key step. The synthesis was completed in 13 steps starting from ethyl 4-chloroacetoacetate with an overall yield of 24%.