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Deep eutectic solvents as suitable solvents for lipase-catalyzed transesterific...

Noro, Jennifer Martins; Cabo, Joana; Freitas, David S.; Roque, Catarina S.; de Castro, Mariana; Cavaco-Paulo, Artur; Silva, C.

In this work, three deep eutectic mixtures (DES 1: choline chloride/urea; DES 2: choline chloride/glycerol; and DES 3: tetrabutylammonium bromide/imidazole) were investigated as mediums for the synthesis of glucose laurate and glucose acetate. Aiming to achieve a greener and more sustainable approach, the synthesis reactions were catalyzed by lipases from Aspergillus oryzae (LAO), Candida rugosa (LCR), and porc...


A short synthesis of (2 S,3 S,4 R )-Dihydroxyhomoprolines from d -Erythrose-Der...

Freitas, David S.; Noro, Jennifer Martins; Drogalin, Artem; Fernandes, Monica C. S.; Baptista, Antonio V. M.; Parente, Joana F. C.

(2S,3S,4R)- Dihydroxyhomoprolines were obtained from a six- carbon- atom lactone intermediate obtained from D- erythrose in a short synthesis, by facile operational methodology, in very good overall yields.


(3S,4R)-3,4-Dihydroxy-N-alkyl-l-homoprolines: synthesis and computational mecha...

Freitas, David S.; Sousa, Cristina E. A.; Parente, Joana; Drogalim, Artem; Fortes, A. Gil; Cerqueira, Nuno M. F. S. A.; Rodríguez-Borges, José E.

This is the first synthetic report of (3S,4R)-dihydroxy-N-alkyl-l-homoprolines described so far. 2,4-O-Benzylidene-d-erythrose was obtained from d-glucose with an improved yield, and then transformed into the title (3S,4R)-dihydroxy-N-alkyl-l-homoprolines, in a two-step strategy, with excellent overall yields. Hydrogenolysis of the benzyl group led to the NH congener. The synthesis of final products from 1,4-la...


Total Stereoselective Michael Addition of N- and S- Nucleophiles to a D-Erythro...

Rocha, Juliana F.; Freitas, David S.; Noro, Jennifer Martins; Silva Teixeira, Carla S.; Sousa, Cristina E. A.; Alves, Maria José Chão

The synthesis of a 1,S-lactone 2,4-O-alkylidene-D-erythrose derivative was found to be a highly stereoselective template in Michael addition trough the reaction of a D-erythrosyl 1,5-lactone derivative with nitrogen and sulfur nucleophiles. The sulfur adducts formed are 1 (D-erythrose derivative):1 (nucleophile), and the nitrogen adducts are 1:2. Both were then treated under HCl to give 2,6-dideoxy-4-functional...


Synthesis of polyhydroxylated pyrrolidines precursors, obtained from D-erythros...

Freitas, David S.; Fortes, A. Gil; Alves, M. José

Iminosugars have demonstrated biological activity in a wide range of enzyme targets, and can be used in the treatment of numerous diseases such as diabetes, obesity, Gaucher disease, cancer, and viral infections, including AIDS. Its activity is due to inhibition, and / or modulating action for a wide range of enzymes that act on protein recognition [1]. Imine of type 1 prepared from D-erythrose 2,4-di-O-protect...


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