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


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.

SUBMITTER: Fairweather JK 

PROVIDER: S-EPMC6268951 | biostudies-literature | 2012 Aug

REPOSITORIES: biostudies-literature

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

Fairweather Jon K JK   Liu Ligong L   Karoli Tomislav T   Ferro Vito V  

Molecules (Basel, Switzerland) 20120815 8


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 de  ...[more]

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