Romano, Domenico
(2016)
Synthesis of novel ribose-based thioimidate n-oxides.
[Laurea magistrale], Università di Bologna, Corso di Studio in
Chimica industriale [LM-DM270]
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Abstract
This work is based on the study of new synthetic paths to obtain thioimidate N-oxides (TINOs) from D-ribose and to study their reactivity with the purpose to obtain ketonitrones. TINOs, aren’t well known molecules, but these enantiomerically pure backbones could be valuable intermediates in the synthesis of novel ketonitrones which are key intermediates in the synthesis of iminosugars. TINOs
were discovered from the study of glucoraphanin, a particular glucosinolate, that unexpectedly cyclized into a TINO after desulfatation, by a spontaneous intramolecular Michael addition. The first part of this work was to synthetize the TINO 3 from D-ribose 1. The key step was the desilylative cyclisation of a suitably functionalized thiohydroximate 2. Based on precedent work developed in the
laboratory, we could obtain the thiohydroximate from D-ribose. We then focused our studies on the cyclisation step trying to find the suitable substituents that could give the TINO in good yield by desilylative cyclisation. The second part of the project is to obtain ketonitrones 4 by palladiumcatalyzed coupling reaction.
Abstract
This work is based on the study of new synthetic paths to obtain thioimidate N-oxides (TINOs) from D-ribose and to study their reactivity with the purpose to obtain ketonitrones. TINOs, aren’t well known molecules, but these enantiomerically pure backbones could be valuable intermediates in the synthesis of novel ketonitrones which are key intermediates in the synthesis of iminosugars. TINOs
were discovered from the study of glucoraphanin, a particular glucosinolate, that unexpectedly cyclized into a TINO after desulfatation, by a spontaneous intramolecular Michael addition. The first part of this work was to synthetize the TINO 3 from D-ribose 1. The key step was the desilylative cyclisation of a suitably functionalized thiohydroximate 2. Based on precedent work developed in the
laboratory, we could obtain the thiohydroximate from D-ribose. We then focused our studies on the cyclisation step trying to find the suitable substituents that could give the TINO in good yield by desilylative cyclisation. The second part of the project is to obtain ketonitrones 4 by palladiumcatalyzed coupling reaction.
Tipologia del documento
Tesi di laurea
(Laurea magistrale)
Autore della tesi
Romano, Domenico
Relatore della tesi
Correlatore della tesi
Scuola
Corso di studio
Parole chiave
d-ribose thiohydroximate TINO Liebeskind-Srogl
Data di discussione della Tesi
22 Marzo 2016
URI
Altri metadati
Tipologia del documento
Tesi di laurea
(NON SPECIFICATO)
Autore della tesi
Romano, Domenico
Relatore della tesi
Correlatore della tesi
Scuola
Corso di studio
Parole chiave
d-ribose thiohydroximate TINO Liebeskind-Srogl
Data di discussione della Tesi
22 Marzo 2016
URI
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