Issue 15, 2015

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

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

Supplementary files

Article information

Article type
Paper
Submitted
04 Nov 2014
Accepted
09 Jan 2015
First published
09 Jan 2015

RSC Adv., 2015,5, 11198-11206

Author version available

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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