195881-29-9

Upstream product

• 195881-17-5 2-cyano-1-phenylethyl carbonochloridate 
• 108787-34-4 bis(N,N-diisopropylamino)-2-(4-nitrophenyl)ethoxyphosphane 
• 195881-26-6 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)guanosine 

Relevant academic research and scientific papers

The (2-cyano-1-phenyl)ethoxycarbonyl (cpeoc) group-a new protecting group for oligoribonucleotide synthesis

The (2- cyano-1-phenyl)ethoxycarbonyl (cpeoc) group was developed as a new base-labile protecting group for the 5-OH function in solid-phase synthesis of oligoribonucleotide by the phosphoramidite approach using the 4- methoxytetrahydropyran-4-yl (mthp) group for 2'-protection. The syntheses of the monomeric building blocks and the first oligoribonucleotides obtained by this approach are described.

Nucleotides. Part LXXIII: Oligoribonucleotide synthesis with the (2-cyano-1-phenylethoxy)carbonyl (2c1peoc) group for the 5′-hydroxy protection

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.