Self-supported solution synthesis of oligosaccharides using thioglycosides donors

We propose here an alternative to the solution synthesis of oligosaccharides based on a polyol multi-glycosylation. This method was illustrated by the successful preparation of a tetraglucoside b (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 15,000), 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.(c) 2022 Elsevier Ltd. All rights reserved.

Automated summary

An alternative method for the synthesis of oligosaccharides based on polyol multi-glycosylation is proposed in this study. The method allows for simple separation based on an increase in molecular mass, without the need for aqueous workup or TLC/detector.