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Synthesis of sulfur-containing analogues of alpha GalNAc (Tn-antigen) and beta Gal1,3 alpha GalNAc (T-antigen)
journal contribution
posted on 2023-06-07, 23:58 authored by Irmgard Wenzl, Norbert Neuwirth, Alexander G Hedenetz, Christian Fiedler, Hansjorg Streicher, Frank M Unger, W SchmidA method for the preparation of thio-analogues of the T- and Tn-antigen was developed. Thus, starting from a known N-acetamido-glucoside derivative, the epidithio analogue of the Tn-antigen was accessible in a four-step reaction sequence. The corresponding epidithio analogue and the thioanhydro derivative of the T-antigen were synthesized starting from a disaccharide derivative. For the preparation of the epidithio analogue the sulfur atoms were introduced via thiocyanates in a stepwise fashion, using mesylate as the leaving group at C-6 and triflate as the leaving group at C-4 in the reducing carbohydrate moiety. The synthesis of the thioanhydro analogue was achieved by introducing a thiocyanate group at C-6 into the glucose moiety, followed by subsequent displacement of a mesylate group at C-4 under inversion of configuration utilizing sodium methoxide.
History
Publication status
- Published
Journal
Chemical Monthly / Monatshefte für ChemieISSN
0026-9247Publisher
Springer VerlagExternal DOI
Issue
4Volume
133Page range
531-540Department affiliated with
- Chemistry Publications
Full text available
- No
Peer reviewed?
- Yes
Legacy Posted Date
2012-02-06Usage metrics
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