Synthesis of derivatives of D-ManAcA : aminosugar component of s. aureus capsular polysaccharides /

Abstract

Convenient methods for the synthesis of amino sugar analogs of N-acetyl-2-amino2- deoxy-D-mannopyranose uronic acid (D-ManAcA) were studied. The parallel synthesis method provided an advantage to the approach of multiple compound synthesis of glycomimetic analogs such as glycosyltriazoles and anomeric glycosyl amides. The starting materials, acyl-protected ~-glycosyl azide compounds, were readily prepared via SN2; the substitution of a glycosyl bromide with N3. The synthesis involves 1,3-dipolar cycloadditions of azides with alkynes, which provided a variety of heterocycles, as well as the Staudinger reaction to produce phosphinimine ylides to generate a desired amide compound using a solid-phase support. According to the results obtained from the above, several cycloaddition reactions provided high yields of compounds. From the Staudinger reactions, high yields of product with several acid chlorides were obtained.