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Molecules 2012, 17(8), 9790-9802; doi:10.3390/molecules17089790
Article

Synthesis of Disaccharides Containing 6-Deoxy-a-L-talose as Potential Heparan Sulfate Mimetics

, ,  and ‡,*
Received: 28 June 2012 / Revised: 5 August 2012 / Accepted: 9 August 2012 / Published: 15 August 2012
(This article belongs to the Special Issue Advances in Carbohydrate Chemistry)
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Abstract

A 6-deoxy-a-L-talopyranoside acceptor was readily prepared from methyl a-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 (a:b = 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.
Keywords: disaccharides; heparan sulfate mimetics; fibroblast growth factors disaccharides; heparan sulfate mimetics; fibroblast growth factors
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Fairweather, J.K.; Liu, L.; Karoli, T.; Ferro, V. Synthesis of Disaccharides Containing 6-Deoxy-a-L-talose as Potential Heparan Sulfate Mimetics. Molecules 2012, 17, 9790-9802.

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