226894-56-0

Upstream product

• 199800-59-4 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-O⁶-<2-(4-nitrophenyl)ethyl>-N²-phthaloylguanosine 
• 199800-46-9 2'-deoxy-O⁶-<2-(4-nitrophenyl)ethyl>-N²-phthaloylguanosine 
• 108310-92-5 2-amino-6-(2-(p-nitrophenyl)ethyloxy)-9-[2'-deoxy-β-D-erythropentofuranosyl]purine diacetate 
• 86137-72-6 2'-deoxy-O⁶-<2-(4-nitrophenyl)ethyl>guanosine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 187674-28-8 {9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-carbamic acid 2-(5-dimethylamino-naphthalene-1-sulfonyl)-ethyl ester 

Downstream Products

• 81144-43-6 5'-O-(p,p'-dimethoxytrityl)-2'-deoxyguanosine 

Relevant academic research and scientific papers

Nucleotides: Part LXI: Phthaloyl strategy: A new concept of oligonucleotide synthesis

A new alternative strategy of oligonucleotide synthesis was developed by use of the phthaloyl protecting group for the exocyclic amino functions of the nucleobases (see 9-12). This approach combines the advantages of cheap and easily accessible monomeric building blocks (see 17- 20), standard machine-aided oligonucleotide synthesis, and a fast deprotection protocol which is orthogonal to the cleavage procedure from the solid support. The crude oligonucleotides show high purity and require, in general, no further chromatographic purification.

Nucleotides. Part L. Aglycone protection by the (2-dansylethoxy)carbonyl (= {2-{5-(dimethylamino)naphthalen-1-yl]sulfonyl}ethoxy}carbonyl; dnseoc) group - A new variation in oligodeoxyribonucleoside synthesis

The (2-dansylethoxy)carbonyl (= {2-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl}ethoxy}carbonyl; dnseoc) group was employed for protection of the amino functions of the aglycone residues. The lactam function of 2'-deoxyguanosine was on the one hand unprotected and on the other hand alkylated at O6 of the aglycone with the 2-(4-nitrophenyl)ethyl (npe) and 2-(phenylsulfonyl)ethyl (pse) group, respectively. The syntheses of monomeric building blocks, both phosphoramidites and nucleoside-functionalized supports, are described for the three common 2'-deoxynucleosides (2'-deoxycytidine, 2'-deoxyadenosine, 2'-deoxyguanosine). As kinetic studies with the tritylated nucleosides showed, the dnseoc group is more labile towards DBU cleavage than the corresponding 2-(4-nitrophenyl)ethyl-(npe) and [2-(4-nitrophenyl)ethoxy]carbonyl(npeoc)-protected analogues. These results were confirmed by the very fast deprotection rate of the dnseoc groups at some oligonucleotides.