Self-supported solution synthesis of oligosaccharides using thioglycosides donors
Synthèse supportée d'oligosaccharides avec des thioglycosides
Résumé
We propose here an alternative to the solution synthesis of oligosaccharides based on a polyol multiglycosylation. This method was illustrated by the successful preparation of a tetraglucoside β (1−> 6) equipped with a propargylic linker, ready for conjugation by click chemistry, using overall 5.6 equiv of thioglycosyl donors. Compared to the reported supported solution syntheses of oligosaccharides; the separation here is not based on a specific label (transferring its solubility properties to whole molecules) but on the increase in molecular mass (from 1500 to 15000), allowing a simple separation on a steric exclusion column. Furthermore, the proposed protocol does not require any aqueous workup and use a yellow tracer to visually follow the separation without TLC nor detector.
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