Stereoselective Synthesis of C,C-Glycosides from exo-Glycals Enabled by Iron-Mediated Hydrogen Atom Transfer | Zendy

Damien Tardieu | Zendy; Marine Desnoyers | Zendy; Claire Laye | Zendy; Damien Hazelard | Zendy; Nicolas Kern | Zendy; Philippe Compain | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

Stereoselective Synthesis of C,C-Glycosides from exo-Glycals Enabled by Iron-Mediated Hydrogen Atom Transfer

Author(s) -

Damien Tardieu,

Marine Desnoyers,

Claire Laye,

Damien Hazelard,

Nicolas Kern,

Philippe Compain

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b02496

Subject(s) - chemistry , stereoselectivity , hydrogen atom , glycoside , stereochemistry , hydrogen , atom (system on chip) , catalysis , combinatorial chemistry , organic chemistry , medicinal chemistry , group (periodic table) , computer science , embedded system

We describe herein a convenient strategy for the construction of C , C -glycoside building blocks via the intermediacy of tertiary pseudoanomeric radicals. Application of an iron-mediated hydrogen atom transfer/Michael-Giese coupling enables the anomeric quaternization of readily available exo -glycals with good to complete stereocontrol in the pyranose and furanose series. Carefully optimized conditions allow the use of challenging trisubstituted derivatives prone to undergo further elaboration to stable neoglycoconjugates. Preliminary results for direc C -disaccharide synthesis are also discussed.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research