Pastore, Antonello
(2010)
SYNTHESIS AND ELABORATION OF MONO- AND OLIGO-SACCHARIDES.
[Tesi di dottorato]
(Inedito)
| 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 |
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| 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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