Synthesis of Sugar-fused GABA-analogs

Frank Schweizer; Albin Otter; Ole Hindsgaul

doi:10.1055/s-2001-18097

Synlett 2001; 2001(11): 1743-1746
DOI: 10.1055/s-2001-18097

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Synthesis of Sugar-fused GABA-analogs

Frank Schweizer^* , Albin Otter, Ole Hindsgaul

^*Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada; Fax + 1(780)4 92 77 05; E-mail: ole.hindsgaul@ualberta.ca

Abstract

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γ-Aminobutyric acid (GABA)-sugar analogs in the form of C-ketosides can be prepared in 4 to 7 steps starting from d- or l-Glucono- and d-Galactono-1,5-lactone. The key step in the synthesis is the trimethylsilyl-trifluoromethanesulfonate (TMS-OTf) promoted C-glycosylation of 2-deoxy-3-ulopyranosonates with trimethylsilyl cyanide. Hydrogenation of the resulting β-cyano esters provides GABA-analogs, which are presented on a sugar scaffold.

carbohydrates - amino acids - glycosides - GABA - C-ketosides

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