83451-16-5

Upstream product

• 39149-80-9 tert-butyl 2-bromopropionate 
• 58581-46-7 C₁₄H₁₉NO₃ 
• 7664-93-9 sulfuric acid 
• 598-72-1 2-Bromopropionic acid 
• 115-11-7 isobutene 
• 1243692-16-1 (S)-tert-butyl 2-(cyanomethylamino)propanoate 
• 13404-22-3 tert-butyl L-alaninate hydrochloride 
• 58581-46-7 N-benzylidenealanine N-oxide tert-butyl ester 

Downstream Products

• 21622-74-2 N-(2-acetoxy-3-phenyl-acryloyl)-N-hydroxy-DL-alanine tert-butyl ester 
• 1432584-72-9 (S,Z)-N-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutylidene)-1-(tert-butoxy)-1-oxopropan-2-amine oxide 
• 1432584-75-2 (S,Z)-N-((R)-2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)propylidene)-1-(tert-butoxy)-1-oxopropan-2-amine oxide 
• 1432584-76-3 (S)-tert-butyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)propanamido)propanoate 
• 84765-39-9 (S)-tert-butyl 2-formamidopropanoate 
• 1432584-77-4 (S,Z)-N-(((S)-1-((benzyloxy)carbonyl)pyrrolidin-2-yl)methylene)-1-(tert-butoxy)-1-oxopropan-2-amine oxide 
• 53935-12-9 (S)-benzyl 2-(((S)-1-(tert-butoxy)-1-oxopropan-2-yl) carbamoyl)pyrrolidine-1-carboxylate 
• 1432584-79-6 (S)-tert-butyl 2-((S)-2,6-bis(((benzyloxy)carbonyl)amino)hexanamido)propanoate 
• 1432584-78-5 (S,Z)-N-((S)-2,6-bis(((benzyloxy)carbonyl)amino)hexylidene)-1-(tert-butoxy)-1-oxopropan-2-amine oxide 
• 1432584-81-0 (S)-tert-butyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(4-methoxyphenyl)propanamido)propanoate 
• 1432584-80-9 (S,Z)-N-((S)-2-(((benzyloxy)carbonyl)amino)-3-(4-methoxyphenyl)propylidene)-1-(tert-butoxy)-1-oxopropan-2-amine oxide 
• 1432584-83-2 (S)-benzyl 5-(((S)-1-(tert-butoxy)-1-oxopropan-2-yl)amino)-4-((tert-butoxycarbonyl)amino)-5-oxopentanoate 
• 1432584-82-1 (S,Z)-N-((S)-5-(benzyloxy)-2-((tert-butoxycarbonyl)amino)-5-oxopentylidene)-1-(tert-butoxy)-1-oxopropan-2-amine oxide 
• 1432584-85-4 (10S,13S)-tert-butyl 6-((benzyloxy)carbonyl)-10-(((benzyloxy)carbonyl)amino)-5-imino-13-methyl-3,11-dioxo-1-phenyl-2-oxa-4,6,12-triazatetradecan-14-oate 

Relevant academic research and scientific papers

Peptide fragment coupling using a continuous-flow photochemical rearrangement of nitrones

Go with the flow: A general approach for amide bond formation by way of a continuous-flow photochemical rearrangement of nitrones was described (see scheme). Simple aryl-alkyl amide bonds as well as complex peptide bonds were constructed efficiently with a residence time less than 20minutes. A tetrapeptide was synthesized in this way and the method could be applied to peptide fragment coupling. Copyright

5-Hydroxy[1,2]oxazinan-3-ones as potential carbapenem and D-ala-D-ala surrogates

The title compounds are amino acids whose nitrogen atom is enclosed in a six-membered cyclic hydroxamate bearing a C5-hydroxyl group. They belong to a proposed new family of antibacterial agents targeted to the penicillin receptor. The glycine and alanine members of the family have been synthesized, as racemates, in seven steps from the four-carbon synthon diketene and the tert-butyl esters of N-hydroxyglycine and N-hydroxyalanine. Numerous alternatives to diketene have also been examined, but these lead mainly to five-membered cyclic hydroxamates. The theoretical considerations that have led to this synthetic programme are discussed in some detail. They include analysis of the structures of natural and unnatural penicillin surrogates, analysis of the penicillin pharmacophore, and a treatment of the chemical reaction with which penicillin blocks bacterial cell wall synthesis. The glycine derivative exhibits marginal but real activity vs. Micrococcus luteus. The alanine derivative, which more closely resembles D-ala-D-ala, is fifty times more active. Two five-membered structural isomers of the glycine derivative are inactive.