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Concurrent Hydrogenation of Three Functional Groups Enables Synthesis of C3′-Homologated Nucleoside Amino Acids

Posted on 2017-07-21 - 20:31
Internucleoside amide linkages are excellent mimics of phosphodiesters in RNA and may be used to optimize the properties of short interfering RNAs. Herein we report a remarkably straightforward, efficient and step economic synthesis of C3′-homologated uridine and adenosine amino acids starting from nucleosides in six steps (31% overall yield) and eight steps (16% overall yield), respectively. The key enabling step is a one-pot multifunctional group transformation including a stereoselective hydrogenation, termed “Global Hydrogenation”.

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