195881-28-8

Basic information

• Product Name: 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
• Synonyms: 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
• CAS NO: 195881-28-8
• Molecular Weight: 1044.02
• Mol File: 195881-28-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 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(CAS DataBase Reference)
• NIST Chemistry Reference: 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(195881-28-8)
• EPA Substance Registry System: 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(195881-28-8)

Safety Data

• Hazardous Substances Data: 195881-28-8(Hazardous Substances Data)

Upstream product

• 73627-97-1 3-hydroxy-3-phenylpropanenitrile 
• 195881-17-5 2-cyano-1-phenylethyl carbonochloridate 
• 108787-34-4 bis(N,N-diisopropylamino)-2-(4-nitrophenyl)ethoxyphosphane 
• 195881-24-4 5'-O-[(2-cyano-1-phenylethoxy)carbonyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 

Relevant articles and documents

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.