209047-51-8

Basic information

• Product Name: N-[4,4',4''-tris(benzoyloxy)trityl]-L-phenylalaninamide
• Synonyms: N-[4,4',4''-tris(benzoyloxy)trityl]-L-phenylalaninamide
• CAS NO: 209047-51-8
• Molecular Weight: 766.85
• Mol File: 209047-51-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-[4,4',4''-tris(benzoyloxy)trityl]-L-phenylalaninamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[4,4',4''-tris(benzoyloxy)trityl]-L-phenylalaninamide(209047-51-8)
• EPA Substance Registry System: N-[4,4',4''-tris(benzoyloxy)trityl]-L-phenylalaninamide(209047-51-8)

Safety Data

• Hazardous Substances Data: 209047-51-8(Hazardous Substances Data)

Upstream product

• 5241-56-5 benzyl [(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]carbamate 
• 5241-58-7 L-Phenylalanine amide 
• 86610-66-4 4,4',4''-tris(benzoyloxy)trityl bromide 

Relevant articles and documents

Synthesis and properties of aminoacylamido-AMP: Chemical optimization for the construction of an N-acyl phosphoramidate linkage

This paper describes the design and synthesis of a new type of aminoacyl-adenylate analogue (aa-AMPN) having an N-acyl phosphoramidate linkage where the oxygen atom of the mixed anhydride bond of aminoacyl-adenylate (aa-AMP) is replaced by an amino group. This new type of aa-AMP analogue is expected to be useful as material for studies on the recognition mechanism of the aminoacylation of tRNA and other biochemical reactions. The condensation of phosphoramidite derivatives of carboxamides with nucleoside derivatives failed, because the activated phosphoramidite derivatives reacted with not only the hydroxyl groups but also another reactive species. An alternative approach was examined by the reaction of 5'-O-phosphoramidite adenosine derivatives with carboxamide derivatives. The TBTr and TSE groups were chosen for protection of the amino group of amino acid amides and the phosphate group, respectively. Detailed studies revealed that the use of 5-(3,5-dinitrophenyl)-1H-tetrazole as an activating catalyst of phosphoramidites resulted in rapid condensation within 10 min to give fully protected aa-AMPN derivatives. No side reaction occurred. Deprotection of these products via a two-step procedure gave aa-AMPN derivatives in good yields. It also turned out that aa-AMPNs thus obtained are stable under both acidic and basic conditions, such as 0.1 M HCl (pH 1.0) and 0.1 M NaOH (pH 13.0).