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.

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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
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article

3,4‐Dicyano‐2,5,6‐Trifluorophenyl Glycosides as Electron‐Deficient Fluoroarene Glycosyl Donors for Chemical Glycosylation

Pintu Kumar Mandal, Ashwani K. Tiwari, Ariza Khanam, Mohan Lal et al.
1 citations
Advanced Synthesis & Catalysis
Carbohydrate Chemistry and Synthesis
0.25
article

3,4‐Dicyano‐2,5,6‐Trifluorophenyl Glycosides as Electron‐Deficient Fluoroarene Glycosyl Donors for Chemical Glycosylation

Pintu Kumar Mandal, Ashwani K. Tiwari, Ariza Khanam, Mohan Lal, Mohammad Ovais
article en
1 citations

Abstract

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.

Advanced Synthesis & CatalysisVol. 367(3)
Central Drug Research Institute (IN), Council of Scientific and Industrial Research (IN), Academy of Scientific and Innovative Research (IN)
Clean water and sanitation
Openalex Percentile: Top 46%
Carbohydrate Chemistry and Synthesis
0.25
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