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Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives.

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

SUBMITTER: Bonaccorsi P

PROVIDER: S-EPMC3869296 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives.

Bonaccorsi Paola P Gioia Maria Luisa Di ML Leggio Antonella A Minuti Lucio L Papalia Teresa T Siciliano Carlo C Temperini Andrea A Barattucci Anna A

Beilstein journal of organic chemistry 20131108

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. ...[more]

PMID: 24367407

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