5-Deoxy glycofuranosides by carboxyl group assisted photoinduced electron transfer deoxygenation

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

TETRAHEDRON

Elsevier

Lugar: New York; Año: 2008 vol. 74 p. 1703 - 1710

0040-4020

In connection with the development of practical methods for the synthesis of deoxy sugars, a photoinduced electron-transfer (PET) reaction using 9-methylcarbazole (MCZ) as photosensitizer was applied to a 2-O-(3-trifluoromethyl)benzoylated derivative of D-galacturonic acid. The carboxylic group efficiently assists the a-deoxygenation, being the required irradiation time significantly shorter than in the absence of it. The photochemical reaction was also used for the deoxygenation of D-glucurono-6,3-lactone derivatives, providing in both cases convenient routes for the synthesis of 5-deoxy-hexofuranosides and intermediate compounds for the synthesis of natural products, avoiding the use of metal hydrides.