Carbohydrate research

Catechuic acid and ethyl 2, 4, 5-trihydroxybenzoate from d-glucose

NN Bhujbal, OP Bande, DD Dhavale

Index: Bhujbal, Namdeo N.; Bande, Omprakash P.; Dhavale, Dilip D. Carbohydrate Research, 2009 , vol. 344, # 6 p. 734 - 738

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Abstract

Synthesis of catechuic acid (1) and ethyl 2, 4, 5-trihydroxybenzoate (2) from d-glucose- derived β-ketoester is described. The polyhydroxylated β-ketoester obtained from the hydrolysis of sugar β-ketoester 3 was subjected to an aldol-type condensation to get 4 that on enolization, dehydration, and hydrogenation afforded ethyl 2, 4, 5-trihydroxybenzoate (2). On the other hand, hydrogenation of aldol product 4 afforded polyhydroxylated keto- ...

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