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A trifluoroacetic acid-labile sulfonate protecting group and its use in the synthesis of a near-IR fluorophore

Pauff, Steven M.
Miller, Stephen C.
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Abstract

Sulfonated molecules exhibit high water solubility, a property that is valuable for many biological applications but often complicates their synthesis and purification. Here we report a sulfonate protecting group that is resistant to nucleophilic attack but readily removed with trifluoroacetic acid (TFA). The use of this protecting group improved the synthesis of a sulfonated near-IR fluorophore and the mild deprotection conditions allowed isolation of the product without requiring chromatography.

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J Org Chem. 2013 Jan 18;78(2):711-6. doi: 10.1021/jo302065u. Epub 2012 Dec 13. Link to article on publisher's site

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10.1021/jo302065u
PubMed ID
23167708
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