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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Kotikam, Venubabu; Rozners, Eriks (2017). Concurrent Hydrogenation of Three Functional Groups
Enables Synthesis of C3′-Homologated Nucleoside Amino Acids. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b01934
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