title: Stereoselective synthesis of fluorinated aminoglycosyl phosphonates.
abstract: We describe the conjugate addition of lithiated difluoromethanephosphonates to a diverse range of nitroglycals as a convenient method for the highly stereoselective synthesis of fluorinated aminoglycosyl phosphonates. Our approach provides opportunities to produce hydrolytically stable mimics of biologically important aminoglycosyl phosphates.
authors.affiliation: Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands. e.ruijter@vu.nl.
authors.forename: Sanne
authors.initials: S
authors.lastname: Bouwman
authors.forename: Romano V A
authors.initials: RV
authors.lastname: Orru
authors.forename: Eelco
authors.initials: E
authors.lastname: Ruijter
mesh_terms: D060326:Chemistry Techniques, Synthetic; D006031:Glycosylation; D054879:Halogenation; D006868:Hydrolysis; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D063065:Organophosphonates