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Optimized synthesis of LNA uracil nucleosides

✍ Scribed by T. Santhosh Kumar; Pawan Kumar; Pawan K. Sharma; Patrick J. Hrdlicka

Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 167 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.09.165

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✦ Synopsis

A short, very high yielding, and practical synthesis of LNA uracil diol 6 has been developed from the easily accessible glycosyl donor 1. The concluding O3 0 -debenzylation of 5 resulted in significant reduction of the uracil moiety with many typical debenzylation conditions, while catalytic transfer hydrogenation using Pd(OH) 2 /C and formic acid largely suppressed this undesired side reaction. Facile access to 6 will allow full exploration of RNA-based LNA-technology applications, including polymerase-catalyzed synthesis of LNA-modified RNA-strands.

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