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

ArticleinThe Journal of Organic Chemistry 78(2) · November 2012with17 Reads
Impact Factor: 4.72 · DOI: 10.1021/jo302065u · Source: PubMed

    Abstract

    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.