Site-Selective Acylation of Pyranosides with Oligopeptide Catalysts

Site-Selective Acylation of Pyranosides with Oligopeptide Catalysts

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) a...

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Veröffentlicht in:Journal of organic chemistry 2021-03, Vol.86 (5), p.3907-3922
Hauptverfasser: Seitz, Alexander, Wende, Raffael C, Roesner, Emily, Niedek, Dominik, Topp, Christopher, Colgan, Avene C, McGarrigle, Eoghan M, Schreiner, Peter R
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container_end_page 3922
container_issue 5
container_start_page 3907
container_title Journal of organic chemistry
container_volume 86
creator Seitz, Alexander
Wende, Raffael C
Roesner, Emily
Niedek, Dominik
Topp, Christopher
Colgan, Avene C
McGarrigle, Eoghan M
Schreiner, Peter R
description 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.
doi_str_mv 10.1021/acs.joc.0c02772
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title Site-Selective Acylation of Pyranosides with Oligopeptide Catalysts
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