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Synthesis of Tri-functional Bis-azide Photoaffinity Probe
journal contribution
posted on 2014-08-10, 00:00 authored by Larry L. Klein, Valentina PetukhovaMethyl 3-azidomethyl-5-azido-benzoate (1b) and its corresponding hydroxymethyl reduction product (1a) have been utilized for the synthesis of valuable nonradioactive photoaffinity probes. Previous preparations of (1a) depend upon a nonselective monoactivation of a bis-1,3-hydroxymethylaryl intermediate, leading to the expected statistical range of products/starting material. We report an alternate synthetic approach to these 1,3,5-trisubstituted molecules using recently described C-H activation and boronate refunctionalization methods.
Funding
This work was financially supported by the Potts Foundation (Grant No. 95440).
History
Publisher Statement
Post print version of article may differ from published version. This is an electronic version of an article published in Synthetic Communications. Synthetic Communications is available online at: http://www.informaworld.com/smpp/ DOI: 10.1080/00397911.2012.697595Publisher
Taylor & FrancisLanguage
- en_US
issn
0039-7911Issue date
2013-08-01Usage metrics
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