Journalartikel

Jahr der Veröffentlichung: 2021

Seiten: 3907-3922

Zeitschrift: The Journal of Organic Chemistry

Bandnummer: 86

Heftnummer: 5

ISSN: 0022-3263

DOI Link: https://doi.org/10.1021/acs.joc.0c02772

Verlag: American Chemical Society

Abstract: 
Herein, we report the oligopeptide-catalyzed site-selective acylation of partially protected monosaccharides. We identified catalysts that invert site-selectivity compared to N-methylimidazole, which was used to determine the intrinsic reactivity, for 4,6-O-protected glucopyranosides (trans-diols) as well as 4,6-O-protected mannopyranosides (cis-diols). The reaction yields up to 81% of the inherently unfavored 2-O-acetylated products with selectivities up to 15:1 using mild reaction conditions. We also determined the influence of protecting groups on the reaction and demonstrate that our protocol is suitable for one-pot reactions with multiple consecutive protection steps.

Harvard-Zitierstil: Seitz, A., Wende, R., Roesner, E., Niedek, D., Topp, C., Colgan, A., et al. (2021) Site-Selective Acylation of Pyranosides with Oligopeptide Catalysts, The Journal of Organic Chemistry, 86(5), pp. 3907-3922. https://doi.org/10.1021/acs.joc.0c02772

APA-Zitierstil: Seitz, A., Wende, R., Roesner, E., Niedek, D., Topp, C., Colgan, A., McGarrigle, E., & Schreiner, P. (2021). Site-Selective Acylation of Pyranosides with Oligopeptide Catalysts. The Journal of Organic Chemistry. 86(5), 3907-3922. https://doi.org/10.1021/acs.joc.0c02772