L-Iduronic acid derivatives as glycosyl donors

Abstract

O-[Methyl (2- O-acetyl-3- O-benzyl-4- O-levulinyl- α, and β l-idopyranosid)uronate] trichloroacetimidate and the corresponding n-pentenyl glycosides are efficient l-iduronic acid glycosyl donors. Both have been used for the high-yielding synthesis of basic disaccharide blocks which are useful for the subsequent synthesis of complex oligosaccharides related to heparin/heparan sulfate, and dermatan sulfate. In contrast, the corresponding thioethyl glycosides, thiophenyl glycosides, and fluoride, did not yield the expected disaccharides.