55501-33-2

Upstream product

• 142683-67-8 benzyl (2-tert-butoxycarbonyl-1-methylhydrazino)acetate 
• 60-34-4 methylhydrazine 
• 5437-45-6 Benzyl bromoacetate 

Downstream Products

• 103321-74-0 benzyl (3S,5R)-<2-<methyl>isoxazolidin-3-yl>acetyl>-1-methylhydrazino>acetate 
• 103321-73-9 benzyl (3R,5R)-<2-<methyl>isoxazolidin-3-yl>acetyl>-1-methylhydrazino>acetate 
• 119961-33-0 (4R,5R)-5-[(R)-2-Benzyloxycarbonylamino-3-(N'-benzyloxycarbonylmethyl-N'-methyl-hydrazinocarbonyl)-propyl]-2,2,4-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 119961-33-0 (4S,5R)-5-[(R)-2-Benzyloxycarbonylamino-3-(N'-benzyloxycarbonylmethyl-N'-methyl-hydrazinocarbonyl)-propyl]-2,2,4-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 119961-33-0 (4S,5S)-5-[(S)-2-Benzyloxycarbonylamino-3-(N'-benzyloxycarbonylmethyl-N'-methyl-hydrazinocarbonyl)-propyl]-2,2,4-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 119138-84-0 [N'-((3R,5R)-3,6-Diazido-5-benzyloxymethoxy-hexanoyl)-N-methyl-hydrazino]-acetic acid benzyl ester 
• 33404-78-3 negamycin 
• 357953-68-5 {N'-[(N'-tert-butoxycarbonyl-N-isopropyl-hydrazino)-acetyl]-N-methyl-hydrazino}-acetic acid benzyl ester 
• 119688-96-9 {N'-[(3R,5R)-3,6-Diazido-5-(tert-butyl-dimethyl-silanyloxy)-hexanoyl]-N-methyl-hydrazino}-acetic acid benzyl ester 
• 1613376-40-1 (3R,5R)-benzyl 3-(2-(2-(2-(benzyloxy)-2-oxoethyl)-2-methylhydrazinyl)-2-oxoethyl)-5-(chloromethyl)isoxazolidine-2-carboxylate 
• 604003-56-7 [N'-(9H-fluoren-9-ylmethoxycarbonyl)-N-methyl-hydrazino]-acetic acid benzyl ester 

Relevant academic research and scientific papers

New building blocks for peptide analogue synthesis: Reduced diaza-β3-dipeptides

Reduction of N-protected aza-β3-amino esters and oxidation of the alcohols afford aza-β3-amino aldehydes. Condensation of unprotected aza-β3-amino esters to the resultant aldehydes leads to hydrazones, which have been conv

N- and C-terminal modifications of negamycin

Negamycin 1 is a bactericidal antibiotic with activity against Gram-negative bacteria, and served as a template in an antibiotic discovery program. An orthogonally protected β-amino acid derivative 3a was synthesized and used in parallel synthesis of negamycin derivatives on solid support. This advanced intermediate was also used for N- and C-terminal modifications using solution-phase methodologies. The N-terminal modifications have resulted in the identification of active analogues, whereas the C-terminal modifications resulted in complete loss of antibacterial activity. The N-methyl negamycin analogue, 19a, inhibits protein synthesis (IC50=2.3 μM), has antibacterial activity (Escherichia coli, MIC=16 μg/mL), and is efficacious in an E. coli murine septicemia model (ED50=16.3 mg/kg).

Palladium(II)-Assisted Difunctionalization of Monoolefins: Total Synthesis of (+)-Negamycin and (-)-5-epi-Negamycin

(+)-Negamycin and (-)-5-epi-negamycin were synthesized by a process involving the palladium(II)-assisted alkylation of an optically active ene carbamate followed by carbonylative coupling to a trialkylvinyltin.The synthesis of (+)-negamycin was completed in 15 steps with an overall yield of 13percent.The synthesis of (-)-5-epi-negamycin was completed in 12 steps with an overall yield of 20percent.In preparing these compounds, a highly diastereoselective reduction of an unsaturated ketone and an efficient intramolecular Mitsunobu reaction were also carried out.