82629-35-4

Upstream product

• 100-52-7 benzaldehyde 
• 101-02-0 triphenyl phosphite 
• 621-84-1 O-benzyl carbamate 
• 3426-89-9 phenyl phosphorodichloridite 
• 75-33-2 2-propanethiol 
• 65164-84-3 O,O-diphenyl {[(benzyloxy)carbonyl]amino}(phenyl)methylphosphonate 

Downstream Products

• 472966-61-3 methyl N-[[{[(benzyloxy)carbonyl]amino}(phenyl)methyl](phenoxy)phosphoryl]-L-valinate 
• 472966-59-9 O-phenyl N-benzyl-P-[{[(benzyloxy)carbonyl]amino}(phenyl)methyl]phosphonamidate 
• 472966-60-2 O-phenyl N-isoamyl-P-[{[(benzyloxy)carbonyl]amino}(phenyl)methyl]phosphonamidate 
• 472966-62-4 O-benzyl O-phenyl {[(benzyloxy)carbonyl]amino}(phenyl)methylphosphonate 
• 472966-58-8 O-phenyl N-phenyl-P-[{[(benzyloxy)carbonyl]amino}(phenyl)methyl]phosphonamidate 

Relevant academic research and scientific papers

A facile synthesis of phenyl hydrogen α-(benzyloxycarbonylamino)benzylphosphonates

A series of phenyl Hydrogen α-(benzyloxycarbonylamino)benzylphosphonates are prepared from the reaction of benzyl carbamate, substituted benzaldehydes and phenoxydichlorophosphine in acetic chloride and subsequent hydrolysis. The reactions proceed smoothly in mild condition and afford the title compounds in good yields.

Synthesis of fluorescent (benzyloxycarbonylamino)(aryl)methylphosphonates

The synthesis of a library of structurally variable aromatic esters of (benzyloxycarbonylamino)(aryl)methylphosphonic acids is described by means of the Oleksyszyn reaction. The library was enlarged by the application of a Suzuki-Miayra approach and by preparation of mixed esters.

Transesterification of monophenyl phosphonamidates - Chemical modelling of serine protease inhibition

O-Phenyl phosphonamidates have been designed to bind covalently by nucleophilic substitution to the serine residue in the active site of serine proteases, similarly to the diphenyl phosphonates used as standard. The synthesis of these compounds as well as their phosphonylating reactivity towards methanol, which served as mimetic of the serine nucleophile, is described. The stereochemistry of the substitution in basic solutions was studied in some detail. The stability of the phosphonamidates in aqueous solutions and their selectivity in the reaction against alcohols versus thiols proved that they constitute a class of potential inhibitors of serine proteases, as well as valuable tools to investigate the mechanism of inhibition.

A convenient method for the synthesis of N-protected 1-aminoalkylphosphonate mixed monothioesters and dithioesters

A series of N-protected 1-aminoalkylphosphonate mixed monothioesters and dithioesters were synthesized using one-pot reactions of benzyl carbamate, aldehydes and alkoxyphosphine dichlorides or alkylthiophosphine dichloride, followed by alcoholysis with thiol or alcohols in the presence of triethylamine.