title: Rapid and selective reduction of amide group by borane-amine complexes in acyl protected nucleosides.
abstract: Borane-amine complexes provide an unusually fast and selective reduction of a deoxynucleoside N-acyl group to a corresponding N-alkyl group. Three different nucleosides (dG, dA, and dC) each having one of three N-protecting groups (benzoyl, isobutyryl, or acetyl) were used to prepare N-alkylated nucleosides in good yields under mild conditions. Deoxyribose O-acyl protecting groups remain intact at the conditions of N-acyl group reduction.
authors.affiliation: Department of Chemistry, Duke University, Durham, NC 27708, USA.
authors.forename: Z A
authors.initials: ZA
authors.lastname: Sergueeva
authors.forename: D S
authors.initials: DS
authors.lastname: Sergueev
authors.forename: B R
authors.initials: BR
authors.lastname: Shaw
mesh_terms: D000577:Amides / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D000577:Amides; D000588:Amines; D001880:Boranes; D009705:Nucleosides