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Beilstein-Institut, Beilstein Journal of Organic Chemistry, (9), p. 2410-2416, 2013

DOI: 10.3762/bjoc.9.278

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Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives

This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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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 β-D-gluco- or galactopyranosides. All products were isolated in good yields and were fully characterized.