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
- Auteurs
- Fiore, Michele, Daskhan Gour Chand, Thomas Baptiste, and Renaudet Olivier
- Revue
- Beilstein J. Org. Chem.
- Volume
- 10
- Pagination
- 1557–1563, 7 pp.
- ISSN
- 1860-5397
Soumis le 12 avril 2018