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Synlett 1998; 1998(12): 1393-1395
DOI: 10.1055/s-1998-1944
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Stereoselective Synthesis of α-C-Glucosamines via Anomeric Organosamarium Reagents

Lise Andersen* , Lise Munch Mikkelsen, Jean-Marie Beau, Troels Skrydstrup
  • *Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark; Fax 45 86 19 61 99; E-mail: ts@kemi.aau.dk
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Publication History

Publication Date:
31 December 2000 (online)

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The direct coupling of the pyridyl sulfone of N-acetylglucosamine with aldehydes or ketones is promoted by samarium diiodide affording the corresponding α-C-glycosides preferentially. A C-disaccharide has been synthesized using this approach.

C-glycosylation - samarium diiodide - pyridyl sulfones - anomeric anions - N-acetyl glucosamine