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 β-D-gluco- or galactopyranosides. All products were isolated in good yields and were fully characterized.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869296 | PMC |
| http://dx.doi.org/10.3762/bjoc.9.278 | DOI Listing |
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Beilstein J Org Chem
December 2013
Dipartimento di Scienze chimiche, Università di Messina, viale F. Stagno d'Alcontres 31, 98166 Messina, Italy.
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 β-D-gluco- or galactopyranosides.
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