GeCl2·Dioxane-AgBF4 Catalyzed Activation of Glycosyl Fluorides for Glycosylation

Qiuyu Zhu; Yu Tang; Biao Yu

doi:10.1021/acs.orglett.2c01146

GeCl₂·Dioxane-AgBF₄ Catalyzed Activation of Glycosyl Fluorides for Glycosylation

Org Lett. 2022 May 27;24(20):3626-3630. doi: 10.1021/acs.orglett.2c01146. Epub 2022 May 12.

Authors

Qiuyu Zhu¹, Yu Tang¹, Biao Yu^{1

2}

Affiliations

¹ State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China.
² School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, China.

PMID: 35549391
DOI: 10.1021/acs.orglett.2c01146

Abstract

A catalytic glycosyl fluoride activation system using the GeCl₂·dioxane-AgBF₄ combination was developed, which involves a reversible activation of the anomeric C-F bond by a [Ge(II)-Cl]⁺ cation and a reversible chloride ion transfer between Ge(II) and glycosyl cations. This catalytic glycosylation system is easy to operate, proceeds at room temperature, and offers a broad scope of substrates.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Dioxanes*
Fluorides* / chemistry
Glycosylation

Substances

Dioxanes
Fluorides