Expedient Synthesis of a Linear Nonadecaarabinofuranoside of the Mycobacterium tuberculosis Cellular Envelope

Abstract

The synthesis of oligosaccharides is demanding as it requires multiple steps and long reaction sequences. The choice of glycosylation method and protecting groups is very important for the successful synthesis of any oligosaccharide. In this paper, we show that ethynylcyclohexyl carbonate glycosyl donors are excellent for the synthesis of a nonadecasaccharide fragment of the Mycobacterium tuberculosis glycocalyx using a split/react/couple strategy. The synthesis of the target nonadecasaccharide was accomplished using eight different reactions and 23 steps in 6.4 % overall yield.