The Synthesis of Glycosyl Amides from Unprotected Carbohydrates and Acylsilanes
We report on a new methodology for the stereoselective synthesis of β-anomeric <i>N</i>-glycosyl amides from unprotected carbohydrates via the reaction of <i>in situ</i> generated carbohydrate oximes with acylsilanes. By variation of the acylsilane, <i>N</i>-glycosyl amides with azide and chloride conjugation handles are prepared in excellent yield and β-selectivity from unprotected sugars.
Authors
- Mattie S. M. Timmer (ORCID: https://orcid.org/0000-0001-7884-0729)
- Amy J. Foster
- Amy T. Lynch (ORCID: https://orcid.org/0000-0001-8669-5998)
- Emma M. Dangerfield (ORCID: https://orcid.org/0000-0001-7731-3951)
- Bridget L. Stocker
Institutions
- Victoria University of Wellington (NZ)
- Sunny BioDiscovery (United States) (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-02-04
- DOI
- https://doi.org/10.1021/acs.orglett.4c04666
- Citations
- 2
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- Marsden Fund