Glycosylation of vicinal di- and trifluorinated glucose and galactose donors
Glycosylation of vicinal di- and trifluorinated glucose and galactose donors
The acid-catalysed formation of glycosidic bonds is more difficult when glycosyl donors are fluorinated, especially at the 2-position. Here we report high-yielding glycosidation and glycosylation reactions of 2,3-difluorinated- and 2,3,4-trifluorinated gluco- and galactopyranoside donors with a variety of acceptors under conventional trichloroacetimidate/TMSOTf activation in moderate to high anomeric selectivities. This methodology allows access to highly fluorinated glycans, illustrated with the synthesis of a pentafluorinated disaccharide.
9082-9085
Huonnic, Kler
095e77fd-6ce1-49df-94c3-584e25a4f2f2
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
28 June 2023
Huonnic, Kler
095e77fd-6ce1-49df-94c3-584e25a4f2f2
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Huonnic, Kler and Linclau, Bruno
(2023)
Glycosylation of vicinal di- and trifluorinated glucose and galactose donors.
ChemComm, 59 (59), .
(doi:10.1039/D3CC02518G).
Abstract
The acid-catalysed formation of glycosidic bonds is more difficult when glycosyl donors are fluorinated, especially at the 2-position. Here we report high-yielding glycosidation and glycosylation reactions of 2,3-difluorinated- and 2,3,4-trifluorinated gluco- and galactopyranoside donors with a variety of acceptors under conventional trichloroacetimidate/TMSOTf activation in moderate to high anomeric selectivities. This methodology allows access to highly fluorinated glycans, illustrated with the synthesis of a pentafluorinated disaccharide.
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d3cc02518g
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Accepted/In Press date: 27 June 2023
e-pub ahead of print date: 28 June 2023
Published date: 28 June 2023
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© 2023 The Royal Society of Chemistry.
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Local EPrints ID: 479006
URI: http://eprints.soton.ac.uk/id/eprint/479006
ISSN: 1359-7345
PURE UUID: 7aa2b4ec-2136-4aca-9528-5c9a2c39238d
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Date deposited: 17 Jul 2023 16:55
Last modified: 18 Mar 2024 02:52
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Author:
Kler Huonnic
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