195881-17-5

Upstream product

• 73627-97-1 3-hydroxy-3-phenylpropanenitrile 
• 503-38-8 trichloromethyl chloroformate 
• 76-02-8 trifluoroacetyl chloride 

Downstream Products

• 195881-20-0 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)uridine 
• 1885-38-7 cinnamic nitrile 
• 24840-05-9 (Z)-cinnamonitrile 
• 649759-77-3 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-O⁴-[2-(4-nitrophenyl)ethyl]-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)uridine 
• 195881-28-8 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-2-(4-nitrophenyl)ethyl diisopropylphosphoramidite 
• 195881-48-2 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytidine 3'-2-(4-nitrophenyl)ethyl diisopropylphosphoramidite 
• 195881-32-4 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 3'-(hydroxy butanedioate) 
• 195881-31-3 5'-O-[(2-cyano-1-pheylethoxy)carbonyl]-N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)cytidine 3'-(hydrogen butanedioate) 
• 195881-45-9 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)uridine 3'-2-(4-nitrophenyl)ethyl diisopropylphosphoramidite 
• 195881-30-2 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl) 3'-(hydrogen butanedioate) 
• 195881-29-9 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 3'-2-(4-nitrophenyl)ethyl diisopropylphosphoramidite 
• 364776-73-8 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]thymidine 
• 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

Nucleosides. Part LXIV. Base-Labile Protecting Groups for the Oligoribonucleotide Synthesis

New labile protecting groups for the anticipated synthesis of oligoribonucleotides were developed and introduced via their carbonochloridates 8-11 at the 5'-O position of thymidine (15) to form 16, 18, 21, and 24 in good yields (Schemes 2 and 3). Similarly, the 5'-O-diphenylphosphinoyl(dpp)-protected thymidine derivative 27 was synthesized with diphenylphosphinoyl chloride 14 as the reactive reagent. With the help of the model compounds 16, 18, 21, 24, and 27, the deprotection rates of these functions towards base treatment were recorded to evaluate their usefulness as temporary protecting groups in RNA assembly (Table). Finally, the relative stability of the 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) protecting group towards bases confirmed its use as a permanent blocking group in our npe/npeoc strategy.

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.