Synthesis of a β‐Ketophosphonate Bioisostere of UDP‐<i>N</i>‐acetylglucosamine

Abstract

Abstract A concise route to a new β‐ketophosphonate analog of glycosyl nucleotides is described. Such a diphosphate bioisostere is a stable mimic of enzyme substrates involved in peptidoglycan biosynthesis and will be the starting point for the development of new potential antibiotics. The synthesis is carried out by condensing a lithiomethylenephosphonate derivative on a methyl N ‐acetylglucosaminylacetate followed by esterification with a uridine derivative. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2009)