5-Deoxy glycofuranosides by carboxyl group assisted photoinduced electron-transfer deoxygenation |
| |
Authors: | Andrea Bordoni |
| |
Institution: | CIHIDECAR (CONICET), Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II, Ciudad Universitaria, 1428 Buenos Aires, Argentina |
| |
Abstract: | 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 α-deoxygenation, the required irradiation time being significantly shorter than that 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 the convenient routes for the synthesis of 5-deoxy-hexofuranosides and intermediate compounds for the synthesis of natural products, avoiding the use of metal hydrides. |
| |
Keywords: | PET deoxygenatin Deoxy sugars Galactofuranosides Glucofuranosides |
本文献已被 ScienceDirect 等数据库收录! |
|