Pastore, Antonello (2010) SYNTHESIS AND ELABORATION OF MONO- AND OLIGO-SACCHARIDES. [Tesi di dottorato] (Inedito)
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| Tipologia del documento: | Tesi di dottorato |
|---|---|
| Lingua: | English |
| Titolo: | SYNTHESIS AND ELABORATION OF MONO- AND OLIGO-SACCHARIDES |
| Autori: | Autore Email Pastore, Antonello antonello.pastore@unina.it |
| Data: | 30 Novembre 2010 |
| Numero di pagine: | 200 |
| Istituzione: | Università degli Studi di Napoli Federico II |
| Dipartimento: | Chimica organica e biochimica |
| Scuola di dottorato: | Scienze chimiche |
| Dottorato: | Scienze chimiche |
| Ciclo di dottorato: | 23 |
| Coordinatore del Corso di dottorato: | nome email Previtera, Lucio previter@unina.it |
| Tutor: | nome email Adinolfi, Matteo adinolfi@unina.it Iadonisi, Alfonso iadonisi@unina.it |
| Data: | 30 Novembre 2010 |
| Numero di pagine: | 200 |
| Parole chiave: | carbohydrates, protecting groups, synthesis of oligosaccharides, regioselectivity, chemoselectivity |
| Settori scientifico-disciplinari del MIUR: | Area 03 - Scienze chimiche > CHIM/06 - Chimica organica |
| Depositato il: | 02 Dic 2010 08:56 |
| Ultima modifica: | 30 Apr 2014 19:45 |
| URI: | http://www.fedoa.unina.it/id/eprint/8212 |
| DOI: | 10.6092/UNINA/FEDOA/8212 |
Abstract
This thesis has been addressed towards several issues of synthetic carbohydrate chemistry. Part of the work has focused on original approaches for the functionalization of mono- and oligo-saccharides through the regioselective de-O-benzylation of protected sugars based on the I2/Et3SiH combined system, the chemoselective removal of a range of alkoxycarbonyl groups from carbinols, and the straightforward access to 2-O-deprotected allyl glycosides by BiBr3-promoted activation of peracetylated glycosyl iodides. In the second part of this work, two different sequential one-pot schemes for the rapid assembly of biologically relevant oligosaccharides have been reported. The first strategy allowed the the straightforward synthesis of the antitumor PI-88 pentasaccharide, while the second one afforded oligosaccharides related to HIV gp120.
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