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Stereoselective Synthesis of 2¿Acetamido-1,2-dideoxyallonojirimycin (DAJNAc), a New Potent Hexosaminidase Inhibitor

AuthorsDe la Fuente, A.; Martín, Rubén ; Mena-Barragán, Teresa; Verdaguer, Xavier; García Fernández, José Manuel ; Ortiz-Mellet, Carmen; Riera, Antoni
Issue Date2013
PublisherAmerican Chemical Society
CitationOrganic Letters 15: 3638- 3641 (2013)
AbstractA practical synthesis of the previously unreported N-acetyl-D-allosamine glycomimetic DAJNAc is described. The reaction sequence involves Pd-catalyzed allylic substitution by phthalimide in an azaheterobicyclic scaffold as the key step. The new iminosugar resulted in being a stronger ß-N-acetylglucosaminidase (human placenta) competitive inhibitor than the D-gluco (DNJNAc) and D-galacto (DGJNAc) stereoisomers.
Identifiersdoi: 10.1021/ol401517x
issn: 1523-7052
Appears in Collections:(IIQ) Artículos
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