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Synlett 2006(20): 3451-3454  
DOI: 10.1055/s-2006-958417
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Stereoselective Synthesis of N-β-d-Glycosyl Amides by a Ritter-type Reaction

Xuezheng Songa, Rawle I. Hollingsworth*a,b
a Department of Chemistry and Biochemistry, Michigan State University, East Lansing, MI 48824, USA
b Department of Molecular Biology, Michigan State University, East Lansing, MI 48824, USA
Fax: +1(517)3539334; e-Mail: rih@cem.msu.edu;
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Publication History

Received 16 February 2006
Publication Date:
08 December 2006 (online)

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Abstract

A facile stereoselective synthesis of protected N-glycosyl amides is reported. Peracetates or perpivaloates of monosaccharides with gluco-, galacto- and manno-configurations react with acetonitrile in a Ritter-like fashion under acidic condition. The stereoselectivity of this anomeric Ritter-type reaction strongly favors β-anomers of N-d-glycosyl amides regardless of the configurations of the sugars.

Key words

Ritter reaction - amidation - glycosyl amide