Solvent-Free and Stereoselective
Synthesis of C-Glycosides by Michael-Type Addition
of Enamino Esters to 2-Nitro-d-glucal

Ti Zhang; Chu-Yi Yu; Zhi-Tang Huang; Yue-Mei Jia

doi:10.1055/s-0030-1258498

LETTER

Solvent-Free and Stereoselective Synthesis of C-Glycosides by Michael-Type Addition of Enamino Esters to 2-Nitro-d-glucal

Ti Zhang^a,b, Chu-Yi Yu*^a, Zhi-Tang Huang*^a, Yue-Mei Jia^a
^a Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
Fax: +86(10)82616433; e-Mail: yucy@iccas.ac.cn;
^b Graduate University of Chinese Academy of Sciences, Beijing 100049, P. R. of China

Abstract

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Abstract

Michael-type addition of enamino esters to 3,4,6-tri-O-benzyl-2-nitro-d-glucal under solvent-free conditions formed C-glycosides in excellent yields with high stereoselectivity. Reduction of the nitro group afforded the corresponding bicyclic 2-amino C-glycosides.

Key words

solvent-free - C-glycosides - Michael-type addition

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References

References and Notes

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