Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives

• Paola Bonaccorsi,
• Maria Luisa Di Gioia,
• Antonella Leggio,
• Lucio Minuti,
• Teresa Papalia,
• Carlo Siciliano,
• Andrea Temperini and
• Anna Barattucci

Beilstein J. Org. Chem. 2013, 9, 2410–2416, doi:10.3762/bjoc.9.278

• fully characterized. Keywords: azide derivatives; click chemistry; glycoconjugates; 2-propyn-1-yl β-D-glycopyranosides; triptycene; Introduction Triptycene (1), with its three arene units fused to the bicyclo[2.2.2]octa-2,5,7-triene system appears as a paddle wheel on closer inspection (Figure 1). The

• as a colorless solid easily purified by column chromatography. Azide acceptors, the 2,3,4,6-tetraacetyl-2-propyn-1-yl-β-D-glycopyranosides 4 and 5 (Scheme 2), were prepared following literature procedures [21][22]. We also decided to subject compound 3 to the cycloaddition with sugar 6 that was