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Keywords:

  • Carbohydrates;
  • Glycomimetics;
  • Sulfur heterocycles;
  • Nucleophilic substitution;
  • Michael addition

Abstract

A short synthesis of thiosugar derivatives mimicking furanose, pyranose, and septanose structures has been achieved starting from L-gulono-1,4-lactone and D-glucoheptono-1,4-lactone. Different strategies used in the synthesis are: (1) a nucleophilic displacement and Michael addition; (2) epoxide ring opening and Michael addition; (3) epoxide ring opening and nucleophilic displacement process; and (4) double nucleophilic displacement. All of these reactions used benzyltriethylammonium tetrathiomolybdate, (BnEt3N)2MoS4 as the sulfur-transfer reagent.