195881-28-8Relevant articles and documents
Nucleotides. Part LXXIII: Oligoribonucleotide synthesis with the (2-cyano-1-phenylethoxy)carbonyl (2c1peoc) group for the 5′-hydroxy protection
Muench, Ursula,Pfleiderer, Wolfgang
, p. 2546 - 2565 (2007/10/03)
The (2-cyano-1-phenylethoxy)carbonyl (2c1peoc) group was developed as a new base-labile protecting group for the 5′-OH function in solid-phase synthesis of oligoribonucleotides via the phosphoramidite approach. The half-lives of its β-elimination process by 0.1M DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) were determined to be 7-14s by HPLC investigations. The 2′-OH function was protected with the acid-labile tetrahydro-4-methoxy-2H-pyran-4-yl (thmp) group, while the 2-(4-nitrophenyl)ethyl (npe) and 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) groups were used for the protection of the base and phosphate moieties. The syntheses of the monomeric building blocks, both phosphoramidites and nucleoside-functionalized supports, as well as the build-up of oligoribonucleotides by means of this approach are described.