Thiomonosaccharide derivatives from D-mannose

Sulfur-containing monosaccharide derivatives can be highly valuable for obtaining compounds with biological activities. In this work, a synthetic route starting from D-mannose has been designed. After a convenient hydroxyl protection and anomeric carbon functionalization in a ciano group, a new carbohydrate analogous has been obtained with sulfur in the ring. The heteroatoms have been introduced by an SN2 mechanism, with subsequent cyclization. Structural identification has been performed by different spectroscopic techniques.