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(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...


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