51549-47-4Relevant academic research and scientific papers
Transprotection of silyl ethers of nucleosides in FeCl3 based ionic liquids
Harjani, Jitendra R.,Nara, Susheel J.,Salunkhe, Manikrao M.,Sanghvi, Yogesh S.
, p. 819 - 822 (2007/10/03)
Ionic liquid mediated deprotection of tert-butyldimethyl silyl (TBDMS) ethers derived from various primary and secondary alcohols have been studied and the reaction conditions optimized. Deprotection of the silyl ethers in FeCl3 based ionic liquids in presence of acetic anhydride yielded the acetate esters of the corresponding alcohols in good yields. The transprotection methodology was extended to the silyl ethers of nucleosides to yield the corresponding acetylated products. Copyright Taylor & Francis, Inc.
Unexpected shift to a 4-imino tautomer upon N4-acylation of 5- methylcytosin-1-yl nucleoside analogues
Busson,Kerremans,Van Aerschot,Peeters,Blaton,Herdewijn
, p. 1079 - 1082 (2007/10/03)
In contrast with the behaviour of 5-unsubstituted cytosine nucleoside analogues, 5-methylcytosine derivatives show upon N4-benzoylation, commonly used as base protection in oligonucleotide synthesis, a tautomeric change of the base moiety from a 4-amino- into a 4-imino isomer. In the latter form, which is easily diagnosticized by 13C NMR and confirmed by X-ray data, the compounds seem to be hydrolytically less stable.
