title: Stereocontrolled syntheses of deoxyribonucleosides via photoinduced electron-transfer deoxygenation of benzoyl-protected ribo- and arabinonucleosides.
abstract: The stereocontrolled, de novo syntheses of beta-2'-deoxy-, alpha-2'-deoxy-, beta-3'-deoxy-, and beta-2', 3'-dideoxyribonucleosides are described. Strategically protected ribose, arabinose, and xylose glycosylation precursors were synthesized bearing C2-esters capable of directing Vorbrüggen glycosylation. The key step is the regioselective deoxygenation of the desired hydroxyl group as either the benzoyl- or 3-(trifluoromethyl)benzoyl derivative. This deoxygenation is accomplished via a photoinduced electron-transfer (PET) mechanism using carbazole derivatives as the photosensitizer. The syntheses of the desired deoxynucleoside generally proceed in three steps from a common, readily available precursor.
authors.affiliation: Department of Chemistry, Box 1822, Station B, Vanderbilt University, Nashville, Tennessee 37235, USA.
authors.forename: Z
authors.initials: Z
authors.lastname: Wang
authors.forename: D R
authors.initials: DR
authors.lastname: Prudhomme
authors.forename: J R
authors.initials: JR
authors.lastname: Buck
authors.forename: M
authors.initials: M
authors.lastname: Park
authors.forename: C J
authors.initials: CJ
authors.lastname: Rizzo
mesh_terms: D001087:Arabinonucleosides / Q000737:chemistry*; D003853:Deoxyribonucleosides / Q000138:chemical synthesis*; D012263:Ribonucleosides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001087:Arabinonucleosides; D003853:Deoxyribonucleosides; D012263:Ribonucleosides