111244-92-9

Upstream product

• 108310-92-5 2-amino-6-(2-(p-nitrophenyl)ethyloxy)-9-[2'-deoxy-β-D-erythropentofuranosyl]purine diacetate 
• 69992-10-5 3',5'-di-O-acetyl-2'-deoxyguanosine 
• 88091-68-3 2-(4-nitrophenyl)ethoxycarbonyl chloride 
• 100-27-6 2-(4-nitrophenyl)ethanol 

Downstream Products

• 156159-75-0 5'-O-(2-dansylethoxycarbonyl)-2'-deoxy-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 
• 148144-80-3 2'-deoxy-5'-O-(monomethoxytrityl)-N²-<2-(4-nitrophenyl)ethoxycarbonyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanosine 
• 199792-82-0 2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 
• 215600-73-0 2-(2-Nitro-phenyl)-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-{6-[2-(4-nitro-phenyl)-ethoxy]-2-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester 
• 215600-76-3 2-(2-Nitro-phenyl)-propane-1-sulfonic acid (2R,3S,5R)-3-hydroxy-5-{6-[2-(4-nitro-phenyl)-ethoxy]-2-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester 
• 215600-75-2 2-(4-Chloro-2-nitro-phenyl)-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-{6-[2-(4-nitro-phenyl)-ethoxy]-2-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester 
• 215600-74-1 2-(2-Chloro-6-nitro-phenyl)-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-{6-[2-(4-nitro-phenyl)-ethoxy]-2-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester 
• 199123-05-2 2-(2,4-Dinitro-phenyl)-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-{6-[2-(4-nitro-phenyl)-ethoxy]-2-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester 
• 131920-31-5 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 
• 199792-99-9 Carbonic acid (2R,3S,5R)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-{6-[2-(4-nitro-phenyl)-ethoxy]-2-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester 2-(5-dimethylamino-naphthalene-1-sulfonyl)-ethyl ester 
• 199793-01-6 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 
• 199792-92-2 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 
• 199793-04-9 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 5'-(2-cyanoethyl diisopropylphosphoramidite) 

Relevant academic research and scientific papers

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.

New 2-(4-nitrophenyl)ethyl(Npe)- and 2-(4- nitrophenyl)ethoxycarbonyl(Npeoc)protected 2'-deoxyribonucleosides and their 3'-phosphoramidites - Versatile building blocks for oligonucleotide synthesis

A series of new base-protected and 5'-O-(4-monomethoxytrityl)- or 5'-O- (4,4'-dimethoxytrityl)-substituted 3'-(2-cyanoethyl diisopropylphosphoramidites) and 3'-[2-(4-nitrophenyl)ethyl diisopropylphosphoramidites] 52-66 and 67-82, respectively, are prepare

Nucleosides. Part LI. The 2-(4-Nitrophenyl)ethoxycarbonyl (npeoc) and 2-(2,4-Dinitrophenyl)ethoxycarbonyl (dnpeoc) Groups for Protection of Hydroxy Functions in Ribonucleosides and 2'-Deoxyribonucleosides

The common 2'-deoxypyrimidine and -purine nucleosides, thymidine (4), O4-thymidine (17), 2'-deoxy-N4-cytidine (26), 2'-deoxy-N6-adenosine (39), and 2'-deoxy-N2--O6-guanosine (52) were further protected by the 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) and the 2-(2,4-dinitrophenyl)ethoxycarbonyl (dnpeoc) group at the OH functions of the sugar moiety to form new partially and fully blocked intermediates for nucleoside and nucleotide syntheses.The corresponding 5'-O-monomethoxytrityl derivatives 5, 18, 30, 40, and 56 were also used as starting material to synthesize some other intermediates which were not obtained by direct acylations.In the ribonucleoside series, the 5'-O-monomethoxytrityl derivatives 14, 36, 49, and 63 reacted with 2-(4-nitrophenyl)ethyl chloroformate (1) to the corresponding 2',3'-bis-carbonates 15, 37, 50, and 64 which were either detritylated to 16, 38, 51, and 65, respectively, or converted by 1,8-diazabicycloundec-7-ene (DBU) treatment to the 2',3'-cyclic carbonates 66-69.The newly synthesized compounds were characterized by elemental analyses and UV and 1H-NMR spectra.