Novel synthesis of methyl 4,6- O-benzylidenespiro[2-deoxy-α- d- arabino-hexopyranoside-2,2′-imidazolidine] and its homologue and sugar-γ-butyrolactam derivatives from methyl 4,6- O-benzylidene-α- d- arabino-hexopyranosid-2-ulose

Abstract

Novel methyl 4,6- O-benzylidenespiro[2-deoxy-α- d- arabino-hexopyranoside-2,2′-imidazolidine] and its homologue methyl 4,6- O-benzylidene-3′,4′,5′,6′-tetrahydro-1′ H-spiro[2-deoxy-α- d- arabino-hexopyranoside-2,2′-pyrimidine] have been synthesized in good yields by reaction of methyl 4,6- O-benzylidene-α- d- arabino-hexopyranosid-2-ulose with 1,2-diaminoethane and 1,3-diaminopropane. The results are completely different from the reaction with arylamines or alkylamines. One-pot synthesis of novel ( E)-methyl 4-[hydroxy (methoxy)methylene]-5-oxo-1-alkyl-(4,6- O-benzylidene-2-deoxy-α- d-glucopyranosido)[3,2- b]pyrrolidines has been achieved by the reaction of alkylamines with the butenolide-containing sugar, derived from the aldol condensation of methyl 4,6- O-benzylidene-α- d- arabino-hexopyranosid-2-ulose with diethyl malonate. These sugar-γ-butyrolactam derivatives are potential GABA receptor ligands.