108492-14-4

Basic information

• Product Name: tert-butyl (S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoate
• Synonyms: tert-butyl (S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoate
• CAS NO: 108492-14-4
• Molecular Weight: 286.331
• Mol File: 108492-14-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: tert-butyl (S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoate(108492-14-4)
• EPA Substance Registry System: tert-butyl (S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoate(108492-14-4)

Safety Data

• Hazardous Substances Data: 108492-14-4(Hazardous Substances Data)

Upstream product

• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 119768-50-2 tert-butyl 2-(R)-(tert-butoxycarbonylamino)-3-bromopropanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 71630-31-4 N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester 
• 124-63-0 methanesulfonyl chloride 
• 90048-49-0 tert-butyl (2S)-2-amino-3-hydroxypropanoate 
• 59859-77-7 2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester 
• 459871-14-8 tert-butyl(2S)-[(tert-butoxycarbonyl)amino]-3-phenylmethanesulfonyloxypropionate 

Downstream Products

• 684270-46-0 (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-azidopropanoic acid 
• 459871-10-4 N^α-(tert-butoxycarbonyl)-N^β-[3(S)-(4-amino-6-carboethoxy-5-methylpyrimidin-2-yl)-1-[(4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl]-2-methylthiopropion-3-yl]-(S)-β-aminoalanine tert-butyl ester 
• 459871-11-5 N^α-(tert-butoxycarbonyl)-N^β-[3(S)-(4-amino-6-carboethoxy-5-methylpyrimidin-2-yl)-1-[(4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl]propion-3-yl]-(S)-β-aminoalanine tert-butyl ester 
• 77215-54-4 tert-butyl 2-<(tert-butoxycarbonyl)amino>-3-aminopropanoate 

Relevant articles and documents

Optimized syntheses of Fmoc azido amino acids for the preparation of azidopeptides

The rise of CuI-catalyzed click chemistry has initiated an increased demand for azido and alkyne derivatives of amino acid as precursors for the synthesis of clicked peptides. However, the use of azido and alkyne amino acids in peptide chemistry is complicated by their high cost. For this reason, we investigated the possibility of the in-house preparation of a set of five Fmoc azido amino acids: β-azido l-alanine and d-alanine, γ-azido l-homoalanine, δ-azido l-ornithine and ω-azido l-lysine. We investigated several reaction pathways described in the literature, suggested several improvements and proposed several alternative routes for the synthesis of these compounds in high purity. Here, we demonstrate that multigram quantities of these Fmoc azido amino acids can be prepared within a week or two and at user-friendly costs. We also incorporated these azido amino acids into several model tripeptides, and we observed the formation of a new elimination product of the azido moiety upon conditions of prolonged couplings with 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate/DIPEA. We hope that our detailed synthetic protocols will inspire some peptide chemists to prepare these Fmoc azido acids in their laboratories and will assist them in avoiding the too extensive costs of azidopeptide syntheses. Experimental procedures and/or analytical data for compounds 3–5, 20, 25, 26, 30 and 43–47 are provided in the supporting information.

Total synthesis of deamido bleomycin A2, the major catabolite of the antitumor agent bleomycin

Metabolic inactivation of the antitumor antibiotic bleomycin is believed to be mediated exclusively via the action of bleomycin hydrolase, a cysteine proteinase that is widely distributed in nature. While the spectrum of antitumor activity exhibited by th