title: L-iduronic acid derivatives as glycosyl donors.
abstract: O-[Methyl (2-O-acetyl-3-O-benzyl-4-O-levulinyl-alpha, and beta-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.
authors.affiliation: Département de Chimie, URA CNRS 1686, Paris, France.
authors.forename: C
authors.initials: C
authors.lastname: Tabeur
authors.forename: F
authors.initials: F
authors.lastname: Machetto
authors.forename: J M
authors.initials: JM
authors.lastname: Mallet
authors.forename: P
authors.initials: P
authors.lastname: Duchaussoy
authors.forename: M
authors.initials: M
authors.lastname: Petitou
authors.forename: P
authors.initials: P
authors.lastname: Sinaÿ
mesh_terms: D002240:Carbohydrate Sequence; D005459:Fluorides / Q000737:chemistry; D006031:Glycosylation; D007067:Iduronic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D008969:Molecular Sequence Data
chemical_list: D007067:Iduronic Acid; D005459:Fluorides