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  • Title: Novel synthesis of methyl 4,6-O-benzylidenespiro[2-deoxy-alpha-D-arabino-hexopyranoside-2,2'-imidazolidine] and its homologue and sugar-gamma-butyrolactam derivatives from methyl 4,6-O-benzylidene-alpha-D-arabino-hexopyranosid-2-ulose.
    Author: Zhang F, Liu H, Li YF, Liu HM.
    Journal: Carbohydr Res; 2010 Apr 19; 345(6):839-43. PubMed ID: 20138258.
    Abstract:
    Novel methyl 4,6-O-benzylidenespiro[2-deoxy-alpha-D-arabino-hexopyranoside-2,2'-imidazolidine] and its homologue methyl 4,6-O-benzylidene-3',4',5',6'-tetrahydro-1'H-spiro[2-deoxy-alpha-D-arabino-hexopyranoside-2,2'-pyrimidine] have been synthesized in good yields by reaction of methyl 4,6-O-benzylidene-alpha-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-alpha-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-alpha-D-arabino-hexopyranosid-2-ulose with diethyl malonate. These sugar-gamma-butyrolactam derivatives are potential GABA receptor ligands.
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