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Aminophosphonic Acids (aminophosphonic + acid)

Distribution by Scientific Domains
Chemistry100%

Selected Abstracts

1-(,-Aminobenzyl)-2-naphthol: A New Chiral Auxiliary for the Synthesis of Enantiopure ,-Aminophosphonic Acids

CHEMISTRY - A EUROPEAN JOURNAL, Issue 27 2009
Kirill
Abstract Ooh Betti! A new diastereoselective synthesis of ,-aminophosphonates has been developed based on the reaction of trialkyl phosphites with chiral imines derived from (R)- or (S)-1-(,-aminobenzyl)-2-naphthol (Betti base; see scheme, X=H, CH3, or Br). The reaction proceeds with high diastereoselectivity. Treatment with HCl results in the formation of the desired ,-aminophosphonic acids. A new diastereoselective synthesis of ,-aminophosphonates has been developed, based on the reaction, in the presence of trifluoroacetic acid, of trialkyl phosphites with chiral imines derived from (R)- or (S)-1-(,-aminobenzyl)-2-naphthol. The reaction proceeds at room temperature in toluene with high diastereoselectivity. The major diastereomer can be separated by crystallization from an appropriate solvent. The relative configuration of both chiral centers of the major diastereomer was determined by single-crystal X-ray structure analysis. The desired ,-aminophosphonic acids can be obtained in enantiopure form by treatment of the corresponding diastereomers with HCl. [source]

Syntheses, characterizations, and crystal structures of phosphonopeptides

HETEROATOM CHEMISTRY, Issue 1 2007
Fang Hua
,-Aminophosphonic acids and their derivatives, as phosphorus analogs of amino acids, have attracted much attention as they show a range of biological activities. In this paper, dialkyl phenyl(4-pyridylcarbonylamino)methylphosphonates were synthesized via the Mannich reaction (Yuan et al., Synthesis 1990, 3, 256) and peptide coupling. Their structures were confirmed by elemental analysis, IR, 1H NMR, 13C NMR, and MS. X-ray diffraction data of compounds (2a, 2b, 2c) were reported respectively. The antibacterial and antitumor activities of these compounds are first reported in this paper. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:9,15, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20244 [source]

Novel routes to aminophosphonic acids: Interaction of dimethyl H-phosphonate with hydroxyalkyl carbamates

HETEROATOM CHEMISTRY, Issue 2 2008
K. Troev
It was found that the reaction of dimethyl H-phosphonate (1) with 2-hydroxyalkyl- N -2,-hydroxyalkyl carbamates at 135°C includes several chemical reaction steps: (i) chemical transformations of 1-methyl-2-hydroxyethyl- N -2,-hydroxyethyl carbamate (2) and 2-methyl-2-hydroxyethyl- N -2,-hydroxyethyl carbamate (3); (ii) transesterification of dimethyl H -phosphonate with 2 and 3, and with secondary hydroxyl-containing compounds that are formed during the course of the chemical transformation of 2-hydroxyalkyl- N -2,-hydroxyalkyl carbamates; (iii) hydrolysis of 1 and dialkyl H-phosphonates, formed via transesterification of 1 with secondary hydroxyl-containing compounds. The interaction was studied by means of 1H, 13C, 31P NMR, and FAB mass spectroscopy. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:119,124, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20404 [source]

1-(,-Aminobenzyl)-2-naphthol: A New Chiral Auxiliary for the Synthesis of Enantiopure ,-Aminophosphonic Acids

CHEMISTRY - A EUROPEAN JOURNAL, Issue 27 2009
Kirill
Abstract Ooh Betti! A new diastereoselective synthesis of ,-aminophosphonates has been developed based on the reaction of trialkyl phosphites with chiral imines derived from (R)- or (S)-1-(,-aminobenzyl)-2-naphthol (Betti base; see scheme, X=H, CH3, or Br). The reaction proceeds with high diastereoselectivity. Treatment with HCl results in the formation of the desired ,-aminophosphonic acids. A new diastereoselective synthesis of ,-aminophosphonates has been developed, based on the reaction, in the presence of trifluoroacetic acid, of trialkyl phosphites with chiral imines derived from (R)- or (S)-1-(,-aminobenzyl)-2-naphthol. The reaction proceeds at room temperature in toluene with high diastereoselectivity. The major diastereomer can be separated by crystallization from an appropriate solvent. The relative configuration of both chiral centers of the major diastereomer was determined by single-crystal X-ray structure analysis. The desired ,-aminophosphonic acids can be obtained in enantiopure form by treatment of the corresponding diastereomers with HCl. [source]