4.4 Article

Self-supported solution synthesis of oligosaccharides using thioglycosides donors

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TETRAHEDRON
卷 125, 期 -, 页码 -

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PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2022.133036

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Glycosylation; Thioglycoside; Odorless thiol; Soluble support synthesis; Oligosaccharides

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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.
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.

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