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Issue 15, 2015
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Introduction of chiral 2-(aminoalkyl) substituents into 5-amino-1,3-oxazol-4-ylphosphonic acid derivatives and their use in phosphonodipeptide synthesis

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Abstract

Starting from phthalimidoalkanoylamines 1 (amino-protected derivatives of L-alanine, L-valine, and L-leucine), we have suggested a straightforward synthetic route to 5-amino-1,3-oxazol-4-ylphosphonic acid derivatives 5 containing a chiral aminoalkyl substituent on the 2-position of the oxazole ring. Compounds 5 have been further used to obtain phosphonodipeptides 8, 9, and 10 with the original optical purity retained.

Graphical abstract: Introduction of chiral 2-(aminoalkyl) substituents into 5-amino-1,3-oxazol-4-ylphosphonic acid derivatives and their use in phosphonodipeptide synthesis

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Publication details

The article was received on 04 Nov 2014, accepted on 09 Jan 2015 and first published on 09 Jan 2015


Article type: Paper
DOI: 10.1039/C4RA13819H
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RSC Adv., 2015,5, 11198-11206

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    Introduction of chiral 2-(aminoalkyl) substituents into 5-amino-1,3-oxazol-4-ylphosphonic acid derivatives and their use in phosphonodipeptide synthesis

    O. I. Lukashuk, E. R. Abdurakhmanova, K. M. Kondratyuk, O. V. Golovchenko, K. V. Khokhlov, V. S. Brovarets and V. P. Kukhar, RSC Adv., 2015, 5, 11198
    DOI: 10.1039/C4RA13819H

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