A trifluoroacetic acid-labile sulfonate protecting group and its use in the synthesis of a near-IR fluorophore
Pauff, Steven M. ; Miller, Stephen C.
Pauff, Steven M.
Miller, Stephen C.
Citations
Altmetric:
Authors
Student Authors
Faculty Advisor
Academic Program
UMass Chan Affiliations
Document Type
Journal Article
Publication Date
2013-01-18
Subject Area
Embargo Expiration Date
Link to Full Text
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.
Source
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
Year of Medical School at Time of Visit
Sponsors
Dates of Travel
DOI
10.1021/jo302065u
Permanent Link to this Item
PubMed ID
23167708