Rapid and selective reduction of amide group by borane-amine complexes in acyl protected nucleosides.
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.
Sergueeva
Z A
ZA
Department of Chemistry, Duke University, Durham, NC 27708, USA.
Sergueev
D S
DS
Shaw
B R
BR
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
D000577:Amides; D000588:Amines; D001880:Boranes; D009705:Nucleosides