Hannah S. Wootton
Adaptable Synthesis of Chondroitin Sulfate Disaccharide Subtypes Preprogrammed for Regiospecific O‐Sulfation
Wootton, Hannah S.; Berry, Sian S.; Ferguson, Elaine L.; Mahon, Clare S.; Miller, Gavin J
Authors
Abstract
A divergent synthetic route to chondroitin sulfate (CS) disaccharide precursors, including rarer subtypes such as CS-D, has been developed. From common intermediates, a series of thioglycoside D-glucosyl donors and 4,6-O-benzylidene protected D-galactosamine acceptors are utilised in a robust glycosylation reaction, achieving β-selectivity and consistent yields (60-75%) on scales >2.0 g. A post-glycosylation oxidation to D-glucuronic acid and orthogonal protecting groups delivers access to CS-A, CS-C, CS-D, CS-E and CS-O precursor subtypes. Of further note is a 4-O-benzyl regioselective reductive ring opening of a 4,6-O-benzylidene protected disaccharide using dichlorophenylborane (PhBCl2) and triethylsilane (Et3SiH) to access a CS-D precursor, in 73% yield over two steps. Finally, synthesis of a 6-O-sulfated CS-C disaccharide containing a conjugable anomeric allyl tether is completed. These materials will provide a benchmark to further synthesise and study chondroitin sulfates.
Citation
Wootton, H. S., Berry, S. S., Ferguson, E. L., Mahon, C. S., & Miller, G. J. (2024). Adaptable Synthesis of Chondroitin Sulfate Disaccharide Subtypes Preprogrammed for Regiospecific O‐Sulfation. European Journal of Organic Chemistry, 27(40), Article e202400587. https://doi.org/10.1002/ejoc.202400587
Journal Article Type | Article |
---|---|
Acceptance Date | Jul 28, 2024 |
Online Publication Date | Jul 29, 2024 |
Publication Date | Oct 21, 2024 |
Deposit Date | Oct 14, 2024 |
Publicly Available Date | Oct 15, 2024 |
Journal | European Journal of Organic Chemistry |
Print ISSN | 1434-193X |
Electronic ISSN | 1099-0690 |
Publisher | Wiley |
Peer Reviewed | Peer Reviewed |
Volume | 27 |
Issue | 40 |
Article Number | e202400587 |
DOI | https://doi.org/10.1002/ejoc.202400587 |
Public URL | https://durham-repository.worktribe.com/output/2957046 |
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Publisher Licence URL
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Published Journal Article
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Publisher Licence URL
http://creativecommons.org/licenses/by/4.0/
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