Orthogonal dual thiol-chloroacetyl and thiol-ene coupling for the sequential one-pot assembly of heteroglycoclusters.

We describe the first one-pot orthogonal strategy to prep. well-defined cyclopeptide-based heteroglycoclusters (hGCs) from glycosyl thiols. Both thiol-chloroactetyl coupling (TCC) and thiol-ene coupling (TEC) have been used to decorate cyclopeptides regioselectively with diverse combination of sugars. We demonstrate that the reaction sequence starting with TCC can be performed one-pot whereas the reverse sequence requires a purifn. step after the TEC reaction. The versatility of this orthogonal strategy has been demonstrated through the synthesis of diverse hGCs displaying alternating binary combinations of $\alpha$-d-Man or $\beta$d-GlcNAc, thus providing rapid access to attractive heteroglycosylated platforms for diverse biol. applications. [on SciFinder(R)]

Références

Titre
Orthogonal dual thiol-chloroacetyl and thiol-ene coupling for the sequential one-pot assembly of heteroglycoclusters.
Type de publication
Article de revue
Année de publication
2014
Revue
Beilstein J. Org. Chem.
Volume
10
Pagination
1557–1563, 7 pp.
ISSN
1860-5397
Soumis le 12 avril 2018