156159-75-0

Upstream product

• 111244-92-9 2'-deoxy-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 

Downstream Products

• 156159-85-2 5'-O-(2-dansylethoxycarbonyl)-2'-deoxy-N²-<2-(4-nitrophenyl)ethoxycarbonyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanosine 3'-<2-(4-nitrophenyl)ethyl N,N-diethylphosphoramidite> 
• 156159-81-8 5'-O-(2-dansylethoxycarbonyl)-2'-deoxy-N²-<2-(4-nitrophenyl)ethoxycarbonyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanosine 3'-<2-(4-nitrophenyl)ethyl N,N-diisopropylphosphoramidite> 
• 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 
• 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 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).

An inverse approach in oligodeoxyribonucleotide synthesis

We synthesized 3'-O-dimetboxytrityl-5'O-phosphoramidites and 5'-O- succinates which can be used as monomeric building blocks for the built up of oligodeoxyribonucleotides in the alternative 5'-3' direction. With this inverse strategy oligonucleotide 3'-conjugates as well as 3'-3' and 5'-5' internucleotidic linkages can be easily formed.

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.