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Bromine‐Promoted Glycosidation of Conformationally Superarmed Thioglycosides
Author(s) -
Panza Matteo,
Civera Monica,
Yasomanee Jagodige P.,
Belvisi Laura,
Demchenko Alexei V.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901969
Subject(s) - chemistry , reactivity (psychology) , stereoselectivity , bromine , nuclear magnetic resonance spectroscopy , glycosylation , organic chemistry , stereochemistry , catalysis , biochemistry , medicine , alternative medicine , pathology
Presented herein is a study of the conformation and reactivity of highly reactive thioglycoside donors. The structural studies have been conducted using NMR spectroscopy and computational methods. The reactivity of these donors has been investigated in bromine‐promoted glycosylations of aliphatic and sugar alcohols. Swift reaction times, high yields, and respectable 1,2‐ cis stereoselectivity were observed in a majority of these glycosylations.