A new class of molecules with a triptycene rigid core surrounded by six monosaccharide residues was synthesized. Hexakis(bromomethyl) substituted triptycene was converted into a six-armed triptycene azide (2,3,6,7,14,15-hexakis(azidomethyl)-9,10-dihydro-9,10-[1',2']benzenoanthracene). The key step of the synthesis was the cycloaddition of the azide to 2-propyn-1-yl beta-D-gluco- or galactopyranosides. All products were isolated in good yields and were fully characterized.
Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives
DI GIOIA, Maria Luisa;LEGGIO, Antonella;SICILIANO, Carlo;
2013-01-01
Abstract
A new class of molecules with a triptycene rigid core surrounded by six monosaccharide residues was synthesized. Hexakis(bromomethyl) substituted triptycene was converted into a six-armed triptycene azide (2,3,6,7,14,15-hexakis(azidomethyl)-9,10-dihydro-9,10-[1',2']benzenoanthracene). The key step of the synthesis was the cycloaddition of the azide to 2-propyn-1-yl beta-D-gluco- or galactopyranosides. All products were isolated in good yields and were fully characterized.File in questo prodotto:
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