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Light-directed radial combinatorial chemistry: orthogonal safety-catch protecting groups for the synthesis of small
Alex Shaginian1, Madhusudan Patel, Mo-Huang Li
1Department of Chemistry, Center for Nanotechnology, University of Wisconsin, Madison, WI 53706, USA.
Abstract:
We describe the development of photolabile protecting groups based on the 3,4,5-trimethoxyphenacyl group (TMP). Orthogonal safety-catches were created by introducing an acid-activatible dimethyl ketal (AA-TMP) and an oxidatively activatible 1,3-dithiane (OA-TMP) into the photolabile TMP group. We demonstrate the application of these protecting groups in light-directed synthesis of small molecule microarrays with diversity elements radially attached to a hydroxyproline scaffold.
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