59191-30-9Relevant academic research and scientific papers
Improved facile synthesis of α-amino phosphonates by the reaction of α-amido sulfones with dialkyl trimethyl silyl phosphites catalyzed by Fe(III) chloride
Veeranjaneyulu, Boyapati,Das, Biswanath
supporting information, p. 449 - 456 (2017/02/24)
An improved efficient synthesis of α-amino phosphonates has been discovered by the reaction of N-benzyloxycarbonylamino sulfones with dialkyl trimethyl silyl phosphites in the presence of FeCl3as a catalyst. The products were formed in high yie
Amidoalkylation of hydrophosphoryl compounds
Dmitriev,Rossinets,Ragulin
experimental part, p. 1092 - 1104 (2011/10/17)
A new mild procedure of the amidoalkylation of hydrophosphoryl compounds in a mixture of acetic anhydride and acetyl chloride was developed as a convenient method of constructing the a-aminophosphoryl fragment of the pseudo-a,a'-dipeptide molecule. The reaction intermediates N,N'-benzylidene- and N,N'-alkylidenebiscarbamates were detected, isolated, and identified. The report presents the results of studying the direct interaction of hydrophosphoryl compounds previously synthesized with biscarbamates in acetic anhydride and other solvents, the influence of the structure of phosphorus component and biscarbamate, and the effect of acid catalysis on the course of this two-component reaction. A new version of the mechanism of the three-component reaction of amidoalkylation of hydrophosphoryl compounds is suggested: it is regarded as a multistage process involving the stage of biscarbamate formation followed by the stage of Arbuzov-type reaction with the intermediate formation of acyliminium cation and P-OAc derivative with trivalent phosphorus. Pleiades Publishing, Ltd., 2011.
A simple and efficient access to α-amino phosphonates from N-benzyloxycarbonylamino sulfones using indium(III) chloride
Das, Biswanath,Damodar, Kongara,Bhunia, Nisith
experimental part, p. 5607 - 5609 (2009/12/06)
(Chemical Equation Presented) Treatment of N-benzyloxycarbonylamino sulfones with triethyl phosphite catalyzed by InCl3 produces the corresponding protected α-amino phosphonates in high yields (71-92%).
Transesterification of monophenyl phosphonamidates - Chemical modelling of serine protease inhibition
Mucha, Artur,Kafarski, Pawe?
, p. 5855 - 5863 (2007/10/03)
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.
The synthesis of N-(β-triphenylgermanyl)-propionyl-α-amino-benzylphosphonates
Ye,Zeng,Liu
, p. 2373 - 2378 (2007/10/03)
A series of N-(β-triphenylgermanyl)propionyl-α-amino-benzylphosphonates was synthesized by reaction of β-triphenylgermanyl propionic acid with α-aminophosphonates under very mild conditions. The structures of products were determined by 1H NMR,
N-H insertion reactions of rhodium carbenoids. Part 1. Preparation of α-amino acid and α-aminophosphonic acid derivatives
Aller, Enrique,Buck, Richard T.,Drysdale, Martin J.,Ferris, Leigh,Haigh, David,Moody, Christopher J.,Pearson, Neil D.,Sanghera, J. Bobby
, p. 2879 - 2884 (2007/10/03)
Rhodium(II) acetate-catalysed decomposition of diazophenylacetates 1 and 3 in the presence of a range of N-H compounds results in an N-H insertion reaction of the intermediate carbenoids and formation of N-substituted phenylglycine derivatives 2 and 4. The corresponding reactions of dimethyl α-diazobenzylphosphonate 5 constitute a simple route to aminophosphonates 6.
