Photoinduced electron-transfer alpha-deoxygenation of aldonolactones. Efficient synthesis of 2-deoxy-D-arabino-hexono-1,4-lactone.
A photoinduced electron-transfer (PET) reaction was used for the deoxygenation at C-2 of aldonolactones derivatized as 2-O-[3-(trifluoromethyl)benzoyl] or benzoyl esters. By irradiation of different D-galactono- and D-glucono-1,4-derivatives, with a 450W lamp, using 9-methylcarbazole as photosensitizer, the corresponding 2-deoxy-D-lyxo- and 2-deoxy-D-arabino-hexono-1,4-lactones were efficiently obtained.
Bordoni
Andrea
A
CIHIDECAR (CONICET), Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina.
de Lederkremer
Rosa M
RM
Marino
Carla
C
D003837:Deoxy Sugars / Q000138:chemical synthesis / Q000737:chemistry; D004579:Electron Transport; D005965:Glucuronates / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry; D010777:Photochemistry / Q000379:methods; D013400:Sugar Acids / Q000138:chemical synthesis* / Q000737:chemistry
C513604:2-deoxy-D-arabino-hexono-1,4-lactone; D003837:Deoxy Sugars; D005965:Glucuronates; D007783:Lactones; D009005:Monosaccharides; D013400:Sugar Acids; C007813:galactonolactone