Novel Synthetic Method of 5-Thioaldopyranosides : Potential Modifier of Biological Functions of Carbohydrate Chains

Abstract

Two new synthetic methods of 5-thioaldopyranosides are described. The first one is substitution of the ring oxygen with sulfur atom via the corresponding acyclic monothioacetals obtained by reaction of pyranoside with dimethylboron bromide and then with thiolacetic acid. Having some limitations in the ring-opening reaction, this method could be applied to disaccharides. The second one is glycosylation with 5-thioaldopyranosyl trichloroacetimidate. Behaviors of synthesized 5-thiopyranoside derivatives toward some glycosidases were also described.