487018-32-6Relevant academic research and scientific papers
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 three-component Mannich-type condensation leading to phosphinic dipeptides-extended transition state analogue inhibitors of aminopeptidases
Dzie?ak, Anna,Pawe?czak, Ma?gorzata,Mucha, Artur
experimental part, p. 3141 - 3145 (2011/06/28)
N-Protected α-aminoalkylphosphinic acids bearing a P-H function were found to be novel practical building blocks in three-component condensations with formaldehyde and secondary amines (amino acids). Such Mannich-type N-phosphonomethylation is a common approach for phosphorus acid derived substrates and leads to multifunctional (phosphonic/amino/carboxylic) compounds of diverse relevance. The utility of this reaction was examined for construction, in a single synthetic step, of advanced phosphinic pseudodipeptides designed to act as extended transition state analogue inhibitors of selected aminopeptidases. Phosphinomethylation of primary amino acids was less efficient and yielded mixtures of products which were separated into individual components, and their structures identified.
α-hydroxy-α-aminophosphinic acids: I. Synthesis of a new analog of phenylglycine and its enantiomers
Rozhko,Ragulun
, p. 533 - 536 (2007/10/03)
Methods for synthesis of a new phosphinic analog of phenylglycine, (α-aminobenzyl)(hydroxy-methyl) phosphinic acid and its enantiomers are developed. 2005 Pleiades Publishing, Inc.
