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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,V. P. Kukhar
RSC Advances Pub Date : 01/09/2015 00:00:00 , DOI:10.1039/C4RA13819H
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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