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 [Tesi di dottorato] (Unpublished)

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Item Type: Tesi di dottorato
Language: English
Title: SYNTHESIS AND ELABORATION OF MONO- AND OLIGO-SACCHARIDES
Creators:
CreatorsEmail
Pastore, Antonelloantonello.pastore@unina.it
Date: 30 November 2010
Number of Pages: 200
Institution: Università degli Studi di Napoli Federico II
Department: Chimica organica e biochimica
Doctoral School: Scienze chimiche
PHD name: Scienze chimiche
PHD cycle: 23
PHD Coordinator:
nameemail
Previtera, Luciopreviter@unina.it
Tutor:
nameemail
Adinolfi, Matteoadinolfi@unina.it
Iadonisi, Alfonsoiadonisi@unina.it
Date: 30 November 2010
Number of Pages: 200
Uncontrolled Keywords: carbohydrates, protecting groups, synthesis of oligosaccharides, regioselectivity, chemoselectivity
MIUR S.S.D.: Area 03 - Scienze chimiche > CHIM/06 - Chimica organica
Date Deposited: 02 Dec 2010 08:56
Last Modified: 30 Apr 2014 19:45
URI: http://www.fedoa.unina.it/id/eprint/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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