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 [Tesi di dottorato] (Unpublished)


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Item Type: Tesi di dottorato
Uncontrolled Keywords: carbohydrates, protecting groups, synthesis of oligosaccharides, regioselectivity, chemoselectivity
Date Deposited: 02 Dec 2010 08:56
Last Modified: 30 Apr 2014 19:45


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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