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Published on: January 13, 2017
The shortest synthetic route to puromycin analogues using a modified Robins approach
Kollappillil S Krishnakumar1, Sébastien Goudedranche, Denis Bouchu
1Laboratoire de Synthèse de Biomolécules (UMR 5246, ICBMS), Université Claude Bernard Lyon 1, 43 boulevard du 11 novembre 1918, 69622 Villeurbanne Cedex, France.
Abstract:
We are reporting on the utility of commercial vinyl isocyanate for a practical synthetic route from adenosine to N(6)-bis-demethylpuromycin in seven steps and 65% overall yield. A clean one-pot conversion of 3'-bromo-2'-carbamoyl derivative 8 to 3'-amino-3'-deoxyadenosine derivative 10 is the main feature of this synthetic pathway. This synthesis is the shortest synthetic route toward 3'-(aminoacylamido)deoxyadenosines to date.
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