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Article

Ferric Chloride Promoted Glycosidation of Alkyl Thioglycosides

by
Lacie M. Ridgway
,
Anupama Das
,
Melanie L. Shadrick
and
Alexei V. Demchenko
*
Department of Chemistry, Saint Louis University, 3501 Laclede Ave., St. Louis, MO 63103, USA
*
Author to whom correspondence should be addressed.
Molecules 2024, 29(20), 4845; https://doi.org/10.3390/molecules29204845
Submission received: 28 August 2024 / Revised: 6 October 2024 / Accepted: 10 October 2024 / Published: 13 October 2024
(This article belongs to the Special Issue Special Issue in Honor of Prof. David Crich’s 65th Birthday for His Outstanding Contributions to Carbohydrate Chemistry)
Versions Notes

Abstract

Reported herein is a new reaction for glycosylation with thioglycosides in the presence of iron(III) chloride. Previously, FeCl3 was used for the activation of thioglycosides as a Lewis acid co-promoter paired with NIS. In the reported process, although 5.0 equiv of FeCl3 are needed to activate thioglycosides most efficiently, no additives were used, and the reactions with reactive glycosyl donors smoothly proceeded to completion in 1 h at 0 °C. This work showcases a new direction in developing glycosylation methods using greener and earth-abundant activators.
Keywords: glycosylation; ferric chloride; green chemistry; carbohydrates; thioglycosides glycosylation; ferric chloride; green chemistry; carbohydrates; thioglycosides

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MDPI and ACS Style

Ridgway, L.M.; Das, A.; Shadrick, M.L.; Demchenko, A.V. Ferric Chloride Promoted Glycosidation of Alkyl Thioglycosides. Molecules 2024, 29, 4845. https://doi.org/10.3390/molecules29204845

AMA Style

Ridgway LM, Das A, Shadrick ML, Demchenko AV. Ferric Chloride Promoted Glycosidation of Alkyl Thioglycosides. Molecules. 2024; 29(20):4845. https://doi.org/10.3390/molecules29204845

Chicago/Turabian Style

Ridgway, Lacie M., Anupama Das, Melanie L. Shadrick, and Alexei V. Demchenko. 2024. "Ferric Chloride Promoted Glycosidation of Alkyl Thioglycosides" Molecules 29, no. 20: 4845. https://doi.org/10.3390/molecules29204845

APA Style

Ridgway, L. M., Das, A., Shadrick, M. L., & Demchenko, A. V. (2024). Ferric Chloride Promoted Glycosidation of Alkyl Thioglycosides. Molecules, 29(20), 4845. https://doi.org/10.3390/molecules29204845

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