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DOI: 10.1055/s-0036-1588510
Unnatural Amino Acid Derivatives through Click Chemistry: Synthesis of Triazolylalanine Analogues
This work was financially supported by the NIH/NIDCR through grant 1RO1DEO23206Publication History
Received: 08 May 2017
Accepted after revision: 26 June 2017
Publication Date:
24 July 2017 (online)
Published as part of the ISHC Conference Special Section
Abstract
A novel tert-butyl 2-(1-oxoisoindolin-2-yl)acetate derivative is selectively alkylated with propargyl bromide in the presence of lithium hexamethyldisilazide. After removal of the tert-butyl protecting group, the resulting N-isoindolinyl (ethynylalanine) derivative is reacted with a series of azides under ‘click conditions’. The click reactions afford an array of N-isoindolinyl- 1,2,3-triazolylalanine derivatives as the free carboxylic acids. Following esterification, the N-isoindolinone protecting group is then transformed into the more easily removable phthaloyl group by selective oxidation at the benzylic position.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588510.
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