Thiosugars are carbohydrate analogues where one or more oxygen atoms are substituted with sulfur in both furanoside and pyranoside structures. Due to the unique conformational and electronic properties conferred by the presence of the sulfur atom, these compounds offer fascinating prospects for medicinal chemistry as glycosidase inhibitors and they have been shown to demonstrate potent biological activity as antiviral, antidiabetic and anticancer compounds. We have developed a highly efficient synthetic methodology to access novel thiosugars by employing intramolecular 'thiol-ene' cyclization reactions. Both 5-exo and 6-endo cyclization pathways have been investigated to access the desired thiosugars. Cyclization reactions occur in high yield with excellent regio- and diastereoselectivity.

Applications of intramolecular thiol-ene reactions for the synthesis of thiosugars

248th National Meeting (2014)

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