title: Low-generation dendrimers with a calixarene core and based on a chiral C(2)-symmetric pyrrolidine as iminosugar mimics.
abstract: The preparation of low-generation dendrimers based on a simple calix[4]arene scaffold by insertion of the iminosugar-analogue C(2)-symmetric 3,4-dihydroxypyrrolidine is described. This methodology allows a rapid incorporation of a considerable number of iminosugar-like moieties in a reduced volume and in a well-defined geometry. The inclusion of alkali-metal ions (sodium and potassium) in the polar cavity defined by the acetamide moieties at the lower rim of the calixarene was demonstrated, which allows also the rigidification of the dendrimer structure and the iminosugar presentation in the clusters. The combination of the supramolecular properties of calixarenes with the advantage of a dendrimeric presentation of repetitive units opens up the possibility of generating well-defined multivalent and multifaceted systems with more complex and/or biologically relevant iminosugars.
authors.affiliation: Dipartimento di Chimica "Ugo Schiff", Università degli Studi di Firenze, via della Lastruccia 13, I-50019 Sesto Fiorentino (Firenze), Italy.
authors.forename: Marco
authors.initials: M
authors.lastname: Marradi
authors.forename: Stefano
authors.initials: S
authors.lastname: Cicchi
authors.forename: Francesco
authors.initials: F
authors.lastname: Sansone
authors.forename: Alessandro
authors.initials: A
authors.lastname: Casnati
authors.forename: Andrea
authors.initials: A
authors.lastname: Goti