Photoinduced electron-transfer alfa-deoxygenation of aldonolactones. Efficient synthesis of 2-deoxy-D-arabino hexono-1,4-lactone.

A. BORDONI; R. M. DE LEDERKREMER; C. MARINO

CARBOHYDRATE RESEARCH

ELSEVIER

Lugar: Nueva York; Año: 2006 vol. 341 p. 1788 - 1795

0008-6215

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 450 W lamp, using 9-methylcarbazole as photosensitizer, the corresponding 2-deoxy-D-lyxo- and 2-deoxy-D-arabino-hexono-1,4-lactones were efficiently obtained.O-[3-(trifluoromethyl)benzoyl] or benzoyl esters. By irradiation of different D-galactono- and D-glucono-1,4-derivatives, with a 450 W lamp, using 9-methylcarbazole as photosensitizer, the corresponding 2-deoxy-D-lyxo- and 2-deoxy-D-arabino-hexono-1,4-lactones were efficiently obtained.D-lyxo- and 2-deoxy-D-arabino-hexono-1,4-lactones were efficiently obtained.