A Trifluoroacetic Acid-labile Sulfonate Protecting Group and Its Use in the Synthesis of a Near-IR Fluorophore

The Journal of Organic Chemistry (Impact Factor: 4.72). 11/2012; 78(2). DOI: 10.1021/jo302065u
Source: PubMed


Sulfonated molecules exhibit high water solubility, a property which 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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