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Synthesis of Tri-functional Bis-azide Photoaffinity Probe

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journal contribution
posted on 10.08.2014 by Larry L. Klein, Valentina Petukhova
Methyl 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: 10.1080/00397911.2012.697595

Publisher

Taylor & Francis

Language

en_US

issn

0039-7911

Issue date

01/08/2013

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