88091-67-2

Basic information

• Product Name: Cytidine, 2'-deoxy-N-[[2-(4-nitrophenyl)ethoxy]carbonyl]-
• CAS NO: 88091-67-2
• Molecular Formula: C18H20N4O8
• Molecular Weight: 420.379
• Mol File: 88091-67-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Cytidine, 2'-deoxy-N-[[2-(4-nitrophenyl)ethoxy]carbonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Cytidine, 2'-deoxy-N-[[2-(4-nitrophenyl)ethoxy]carbonyl]-(88091-67-2)
• EPA Substance Registry System: Cytidine, 2'-deoxy-N-[[2-(4-nitrophenyl)ethoxy]carbonyl]-(88091-67-2)

Safety Data

• Hazardous Substances Data: 88091-67-2(Hazardous Substances Data)

Upstream product

• 100-27-6 2-(4-nitrophenyl)ethanol 
• 88091-66-1 1-(p-nitrophenylethoxycarbonyl)-benzotriazole 
• 951-77-9 2'-Deoxycytidine 

Downstream Products

• 91592-91-5 2'-deoxy-5'-O-(4-monomethoxytrityl)-N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]cytidine 
• 91592-92-6 5'-O-monomethoxytrityl-N⁴-p-nitrophenylethoxycarbonyl-2'-deoxycytidine-3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphate 
• 91592-93-7 N⁴-p-nitrophenylethoxycarbonyl-2'-deoxycytidine-3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphate 
• 91592-95-9 triethylammonium 5'-O-monomethoxytrityl-N⁴-p-nitrophenylethoxycarbonyl-2'-deoxycytidine-3'-p-nitrophenylethyl-phosphate 
• 109205-75-6 {1-[(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid 2-(4-nitro-phenyl)-ethyl ester 
• 102434-70-8 4-Amino-1-[(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1H-pyrimidin-2-one 
• 199792-96-6 Carbonic acid (2R,3S,5R)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-{4-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-2-oxo-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethyl ester 2-(5-dimethylamino-naphthalene-1-sulfonyl)-ethyl ester 
• 199793-02-7 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}cytidine 5'-(2-cyanoethyl diisopropylphosphoramidite) 
• 199793-05-0 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}cytidine 5'-(hydrogen butanedioate) 
• 199792-89-7 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}cytidine 
• 151170-92-2 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}cytidine 
• 215600-68-3 2-(2,4-Dinitro-phenyl)-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-{4-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-2-oxo-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethyl ester 
• 215600-64-9 2-(2-Chloro-6-nitro-phenyl)-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-{4-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-2-oxo-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethyl ester 
• 199123-01-8 2-(4-Chloro-2-nitro-phenyl)-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-{4-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-2-oxo-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethyl ester 

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.

THE USE OF THE p-NITROPHENYLETHOXYCARBONYL GROUP FOR AMINO PROTECTION IN CYTIDINE AND ADENOSINE CHEMISTRY

Amino protection in 2'-deoxycytidine (1) and cytidine (2) as well as in 2'-deoxyadenosine (8) and adenosine (9) respectively can be achieved by the new reagents 1-(p-nitrophenylethoxycarbonyl)-benzotriazole (3) and 1-methyl-3-(p-nitrophenylethoxycarbonyl)-imidazolium chloride (7) to from the corresponding carbamates (4, 5, 13, 14) in high yields.