Synthesis of derivatives of muramic acid and C-1 homologated α-D-glucose as potential inhibitors of bacterial transglycosylase

Abstract

Phosphate derivatives of muramic acid, incorporating a lipid-like group, have been synthesised as potential inhibitors of bacterial transglycosylase. The Lewis acid catalysed addition of unsaturated alkyl silanes to methyl α-D-glucopyranoside, followed by an oxidative cleavage, has been used to provide a route to C-1 homologues of glucose. Conversion of α-D-glucose methanephosphonic acid to esters derived from lipid-like groups is also described.