L-Iduronic acid derivatives as glycosyl donors

Article abstract of DOI:10.1016/0008-6215(95)00346-0

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.