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Molecules. 2012 Aug 15;17(8):9790-802. doi: 10.3390/molecules17089790.

Synthesis of disaccharides containing 6-deoxy-α-L-talose as potential heparan sulfate mimetics.

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1
Drug Design Group, Progen Pharmaceuticals Ltd, Brisbane QLD 4076, Australia. v.ferro@uq.edu.au

Abstract

A 6-deoxy-α-L-talopyranoside acceptor was readily prepared from methyl α-L-rhamnopyranoside and glycosylated with thiogalactoside donors using NIS/TfOH as the promoter to give good yields of the desired a-linked disaccharide (69-90%). Glycosylation with a 2-azido-2-deoxy-D-glucosyl trichloroacetimidate donor was not completely stereoselective (α:β = 6:1), but the desired a-linked disaccharide could be isolated in good overall yield (60%) following conversion into its corresponding tribenzoate derivative. The disaccharides were designed to mimic the heparan sulfate (HS) disaccharide GlcN(2S,6S)-IdoA(2S). However, the intermediates readily derived from these disaccharides were not stable to the sulfonation/deacylation conditions required for their conversion into the target HS mimetics.

PMID:
22895025
DOI:
10.3390/molecules17089790
[Indexed for MEDLINE]
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