A series of 3-thioglycosylated 5,6-diacetoxyindole derivatives, which are important tools for eumelanin research and application, were prepared through a practical and efficient approach exploiting a dynamic mixture of thioglycoside agents. The strategy is feasible for installing both mono- and disaccharide units and relies on the facile in situ conversion of glycosyl disulfides into the corresponding, more reactive, phenylselenenyl sulfides in the presence of diphenyl diselenide, N-bromosuccinimide (NBS) and tetrabutylammonium bromide (TBAB).

Glycosylated eumelanin building blocks by thioglycosylation of 5,6-diacetoxyindole with an expedient selenium-based dynamic-mixture methodology

M. ADINOLFI;
2012

Abstract

A series of 3-thioglycosylated 5,6-diacetoxyindole derivatives, which are important tools for eumelanin research and application, were prepared through a practical and efficient approach exploiting a dynamic mixture of thioglycoside agents. The strategy is feasible for installing both mono- and disaccharide units and relies on the facile in situ conversion of glycosyl disulfides into the corresponding, more reactive, phenylselenenyl sulfides in the presence of diphenyl diselenide, N-bromosuccinimide (NBS) and tetrabutylammonium bromide (TBAB).
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11384/84288
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