156159-70-5

Basic information

• Product Name: 5'-O-(2-dansylethoxycarbonyl)-2'-deoxy-N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]cytidine
• Synonyms: 5'-O-(2-dansylethoxycarbonyl)-2'-deoxy-N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]cytidine
• CAS NO: 156159-70-5
• Molecular Weight: 725.733
• Mol File: 156159-70-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5'-O-(2-dansylethoxycarbonyl)-2'-deoxy-N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]cytidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(2-dansylethoxycarbonyl)-2'-deoxy-N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]cytidine(156159-70-5)
• EPA Substance Registry System: 5'-O-(2-dansylethoxycarbonyl)-2'-deoxy-N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]cytidine(156159-70-5)

Safety Data

• Hazardous Substances Data: 156159-70-5(Hazardous Substances Data)

Upstream product

• 88091-67-2 2'-deoxy-N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}cytidine 

Downstream Products

• 156159-79-4 5'-O-(2-dansylethoxycarbonyl)-2'-deoxy-N⁴-<2-(4-nitrophenyl)ethoxycarbonyl>cytidine 3'-<2-(4-nitrophenyl)ethyl N,N-diisopropylphosphoramidite> 
• 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) 
• 151170-92-2 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N⁴-{[2-(4-nitrophenyl)ethoxy]carbonyl}cytidine 
• 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 
• 156159-83-0 5'-O-(2-dansylethoxycarbonyl)-2'-deoxy-N⁴-<2-(4-nitrophenyl)ethoxycarbonyl>cytidine 3'-<2-(4-nitrophenyl)ethyl N,N-diethylphosphoramidite> 
• 156159-87-4 5'-O-(2-dansylethoxycarbonyl)-2'-deoxy-N⁴-<2-(4-nitrophenyl)ethoxycarbonyl>-3'-O-succinylcytidine 

Relevant articles and documents

Nucleotides. Part LXV. Synthesis of 2'-Deoxyribonucleoside 5'-Phosphoramidites: New Building Blocks for the Inverse (5'-3')-Oligonucleotide Approach

The syntheses of the 3'-O-(4,4'-dimethoxytrityl)-protected 5'-phosphoramidites 25-28 and 5'-(hydrogen succinates) 29-32, which can be used as monomeric building blocks for the inverse (5'-3')-oligodeoxyribonucleotide synthesis are described (Scheme). These activated nucleosides and nucleotides were obtained by two slightly different four-step syntheses starting with the base-protected nucleosides 13-20. For the protection of the aglycon residues, the well-established 2-(4-nitrophenyl)ethyl (npe) and [2-(4-nitrophenyl)ethoxy]carbonyl (npeoc) groups were used. The assembly of the oligonucleotides required a slightly increased coupling time of 3 min in application of the common protocol (see Table 1). The use of pyridinium hydrochloride as an activator (instead of 1H-tetrazole) resulted in an extremely shorter activation time of 30 seconds. We established the efficiency of this inverse strategy by the synthesis of the oligonucleotide 3'-conjugates 33 and 34 which carry lipophilic caps derived from cholesterol and vitamin E, respectively, as well as by the formation of (3'-3')- and (5'-5')-internucleotide linkages (see Table 2).

The 2-Dansylethoxycarbonyl (=2-{[5-dimethylamino)naphthalen-1-yl]sulfonyl}ethoxycarbonyl; Dnseoc) group for protection of the 5'-hydroxy function in oligodeoxyribonucleotide synthesis

Use of the 2-dansylethoxycarbonyl (=2-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl])ethoxycarbonyl; Dnseoc) group as an intermediate 5'-OH protecting group in oligodeoxyribonucleotide synthesis using the automated phosphoramidite approach is described in a model study to an alternative strategy in RNA synthesis.