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- Title
Protection of the 2′-Hydroxy Function of Ribonucleosides as an Iminooxymethyl Propanoate and Its 2′- O-Deprotection through an Intramolecular Decarboxylative Elimination Process.
- Authors
Cieślak, Jacek; Grajkowski, Andrzej; Ausín, Cristina; Beaucage, Serge L.
- Abstract
The design and implementation of 2′-hydroxy protecting groups for ribonucleosides is still a daunting challenge to overcome when assembling RNA (ribonucleic acid) sequences for therapeutic applications. The reaction of 2′- O-aminooxymethylribonucleosides with ethyl pyruvate results in the formation of 2′- O-iminooxymethyl ethyl propanoates. The cleavage of this type of 2′- O-protecting groups is demonstrated through saponification of the esters to 2′- O-iminooxymethyl propanoate salts, which, when needed, decarboxylate quantitatively at 55 °C in the presence of tetra- n-butylammonium fluoride or chloride in dimethyl sulfoxide (DMSO) to produce all four native ribonucleosides.
- Subjects
RIBONUCLEOSIDES; HYDROXYL group; PROPIONIC acid; RNA; ELIMINATION reactions; DECARBOXYLATION; SAPONIFICATION; DIMETHYL sulfoxide
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 35, p5817
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201601308