Document Type
Article
Keywords
carbohydrates, ferric chloride, glycosylation, green chemistry, thioglycosides
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.
Publication Date
10-1-2024
Publication Title
Molecules
E-ISSN
14203049
Volume
29
Issue
20
Original Article Number
4845
Rights
CC BY
DOI
10.3390/molecules29204845
PubMed ID
39459213
Funding Number
GM152125
Funding Sponsor
National Institute of General Medical Sciences
Recommended Citation
Ridgway, Lacie M.; Das, Anupama; Shadrick, Melanie L.; and Demchenko, Alexei V., "Ferric Chloride Promoted Glycosidation of Alkyl Thioglycosides" (2024). Chemistry & Biochemistry Faculty Works. 99.
DOI: https://doi.org/10.3390/molecules29204845
Available at:
https://irl.umsl.edu/chemistry-faculty/99