Acid Catalyzed Stereocontrolled Ferrier-Type Glycosylation Assisted by Perfluorinated Solvent

Lu，Zhiqiang1,2; Li，Yanzhi1,2; Xiang，Shaohua3; Zuo，Mengke1; Sun，Yangxing2; Jiang，Xingxing1,2; Jiao，Rongkai1; Wang，Yinghong1; Fu，Yuqin1

2022-11-01

10.3390/molecules27217234

Molecules   Impact Factor & Quartile

1420-3049

Described herein is the first application of perfluorinated solvent in the stereoselective formation of O-/S-glycosidic linkages that occurs via a Ferrier rearrangement of acetylated glycals. In this system, the weak interactions between perfluoro-n-hexane and substrates could augment the reactivity and stereocontrol. The initiation of transformation requires only an extremely low loading of resin-H and the mild conditions enable the accommodation of a broad spectrum of glycal donors and acceptors. The ‘green’ feature of this chemistry is demonstrated by low toxicity and easy recovery of the medium, as well as operational simplicity in product isolation.

Ferrier rearrangement glycosylation high stereoselectivity perfluorinated solvent reusability

SCI

English

Corresponding

Henan Provincial Science and Technology Research Project[212102210549];Natural Science Foundation of Henan Province[212300410374];National Natural Science Foundation of China[21801112];Shenzhen Fundamental Research and Discipline Layout project[JCYJ20180305123508258];National Natural Science Foundation of China[U1304206];

Biochemistry & Molecular Biology ; Chemistry

Biochemistry & Molecular Biology ; Chemistry, Multidisciplinary

WOS:000881582900001

MDPI

CHEMISTRY

2-s2.0-85141593661

Scopus

1.College of Chemistry and Chemical Engineering and Henan Key Laboratory of Function-Oriented Porous Materials,Luoyang Normal University,Luoyang,471934,China
2.Hubei Key Laboratory of Natural Products Research and Development,Key Laboratory of Functional Yeast (China National Light Industry),College of Biological and Pharmaceutical Sciences,China Three Gorges University,Yichang,443002,China
3.Academy for Advanced Interdisciplinary Studies,Southern University of Science and Technology,Shenzhen,518055,China

Lu，Zhiqiang,Li，Yanzhi,Xiang，Shaohua,et al. Acid Catalyzed Stereocontrolled Ferrier-Type Glycosylation Assisted by Perfluorinated Solvent[J]. Molecules,2022,27(21).

Lu，Zhiqiang.,Li，Yanzhi.,Xiang，Shaohua.,Zuo，Mengke.,Sun，Yangxing.,...&Fu，Yuqin.(2022).Acid Catalyzed Stereocontrolled Ferrier-Type Glycosylation Assisted by Perfluorinated Solvent.Molecules,27(21).

Lu，Zhiqiang,et al."Acid Catalyzed Stereocontrolled Ferrier-Type Glycosylation Assisted by Perfluorinated Solvent".Molecules 27.21(2022).