Obtenção de aza-açucares a partir de D-glucitol

AUTOR(ES)
DATA DE PUBLICAÇÃO

1996

RESUMO

The azasugars (polyhydroxilated pyperidines and pyrrolidines) constitute an important class of natural and synthetic products, due to their ability to inhibit glycosidases, which are enzymes responsible for the cleavage of glycosidic bonds. Inhibition of glycosidases could be of therapeutic value for the treatment of diabetes, cancer, obesity and viral infections. This work presents a route for the preparation of these compounds using D-glucitol, a derivative of D-glucose reduction, as the starting material. 1,2:3,4:5,6-tri-O-isopropilydene-D-Glucitol, 1,2:5,6-di-O-isopropilydene-D-Glucitol and 2,3:5,6-di-O-isopropilydene-D-Glucitol were obtained from the reaction of D-Glucitol with 2,2-dimethoxypropane in moderate yields. Tosylate and azide isopropylidene derivatives of 2,3:5,6-di-O-isopropilydene-D-Glucitol were prepared by a sequence of several selective protection/deprotection and nucleophilic substitution reactions. Formation of an epoxide intermediate and its subsequent ring-opening via intramolecular nucleophilic substitution leads to the synthesis of the heterocyclic 1,5-dideoxy-1,5-diamine-2,3-O-isopropilydene-6-silil-D-Glucitol, which is a precursor of deoxynojirimycin. Therefore, in nine steps, the formal synthesis of deoxynojirimycin was obtaneid.

ASSUNTO(S)

sorbitol glicose açucar

ACESSO AO ARTIGO

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