3,4‐Dicyano‐2,5,6‐Trifluorophenyl Glycosides as Electron‐Deficient Fluoroarene Glycosyl Donors for Chemical Glycosylation
Abstract Here, we present 3,4‐dicyano‐2,5,6‐trifluorophenyl glycosides as bench‐stable, and reactive electron‐deficient fluoroarene based glycosyl donors that can be prepared in one‐step and be activated with catalytic amounts of TMSOTf. The glycosylation reaction conditions show tolerance towards acid/base sensitive protecting groups and have a different substrate scope with 68–89% yields. The electron‐deficient fluoroarene‐containing glycosyl donor enables the construction of O‐ and C ‐glycosides using both free alcohols and silylated alcohols, as well as C ‐ nucleophiles as acceptors.
Authors
- Pintu Kumar Mandal (ORCID: https://orcid.org/0000-0002-5813-9756)
- Ashwani K. Tiwari (ORCID: https://orcid.org/0000-0002-7083-7709)
- Ariza Khanam
- Mohan Lal (ORCID: https://orcid.org/0000-0001-6995-3377)
- Mohammad Ovais
Institutions
- Central Drug Research Institute (IN)
- Council of Scientific and Industrial Research (IN)
- Academy of Scientific and Innovative Research (IN)
Publication Details
- Journal
- Advanced Synthesis & Catalysis
- Published
- 2024-11-26
- DOI
- https://doi.org/10.1002/adsc.202401196
- Citations
- 1
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.25