TY - JOUR A1 - Marradi, Marco A1 - Cicchi, Stefano A1 - Sansone, Francesco A1 - Casnati, Alessandro A1 - Goti, Andrea T1 - Low-generation dendrimers with a calixarene core and based on a chiral C2-symmetric pyrrolidine as iminosugar mimics JF - Beilstein Journal of Organic Chemistry PY - 2012/// VL - 8 SP - 951 EP - 957 SN - 1860-5397 DO - 10.3762/bjoc.8.107 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.8.107 KW - calixarenes KW - cation-responsive system KW - dendrimers KW - iminosugars KW - multivalency N2 - The preparation of low-generation dendrimers based on a simple calix[4]arene scaffold by insertion of the iminosugar-analogue C2-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. ER -