Synthesis of GABOB and GABOB-based chiral units possessing distinct protecting groups (CROSBI ID 197655)
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Podaci o odgovornosti
Ivšić, Trpimir ; Dokli, Irena ; Rimac, Ana ; Hameršak, Zdenko
engleski
Synthesis of GABOB and GABOB-based chiral units possessing distinct protecting groups
In addition to the varied biological activity of GABOB (4-amino-3-hydroxybutanoic acid), the structure of its protected derivatives makes them interesting chiral intermediates for the synthesis of more complex compounds. A stereoselective route to GABOB derivatives with three different protecting groups is presented, using anhydride desymmetrization as a chirality-inducing step. Selective removal of the protecting groups gave compounds with a free carboxylic acid or hydroxy group. Removal of all of the protecting groups allowed GABOB to be isolated in good yield and with excellent ee.
synthetic methods; asymmetric synthesis; anhydrides; amino acids; protecting groups; alkylation
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