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Glycosylated Eumelanin Building Blocks by Thioglycosylation of 5,6‐Diacetoxyindole with an Expedient Selenium‐Based Dynamic‐Mixture Methodology
Author(s) -
Adinolfi Matteo,
d'Ischia Marco,
Iadonisi Alfonso,
Leone Loredana,
Pezzella Alessandro,
Valerio Silvia
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200299
Subject(s) - chemistry , diselenide , diphenyl diselenide , selenium , disaccharide , combinatorial chemistry , bromide , glycosyl , organic chemistry
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).