Late-Stage Oxime <i>O</i>-Glycosylation with Unprotected Glycosyl Fluorides
Herein, we report a straightforward approach to the late-stage oxime <i>O</i>-glycosylation, utilizing unprotected glycosyl fluoride donors under basic aqueous conditions. By employing a diverse array of commercially available aryl/alkyl oximes and modified sugar/steroid oximes, we have successfully synthesized the desired <i>N</i>-<i>O</i>-linked glycosides and oligosaccharides in satisfactory yields, while achieving specific 1,2-<i>trans</i>-selectivity. This approach stands out due to its broad substrate compatibility, capability for gram-scale synthesis, and potential for glyco-diversification of bioactive molecules, thus holding promise for applications in biological and pharmaceutical research.
Authors
- Peng Hui Xu (ORCID: https://orcid.org/0000-0002-9593-7167)
- Yulin Gong
- Biao Yu (ORCID: https://orcid.org/0000-0002-3607-578X)
- Weizhun Yang (ORCID: https://orcid.org/0000-0001-5522-4026)
- Haoyu Zhou (ORCID: https://orcid.org/0000-0001-9751-6246)
- Ruiqiang Zhao
Institutions
- Chinese Academy of Sciences (CN)
- Shanghai Institute of Organic Chemistry (CN)
- University of Chinese Academy of Sciences (CN)
- Shanghai Institute of Technology (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-06-09
- DOI
- https://doi.org/10.1021/acs.orglett.5c02018
- Citations
- 4
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- National Natural Science Foundation of China
- Chinese Academy of Sciences
- Science and Technology Commission of Shanghai Municipality
- National Key Research and Development Program of China