112154-53-7

Upstream product

• 1256244-57-1 N₂-isobutyryl-1,N₂-[1,2-di(isobutyryloxy)ethylene]-2'-deoxyguanosine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 112154-51-5 5'-O-(4,4'-dimethoxytrityl)-3'-O-(2,2,2-trichloroethoxycarbonyl)-N²-isobutyryldeoxyguanosine 
• 68892-41-1 5'-O-dimethoxytrityl-N-isobutyryldeoxyguanosine 
• 112154-52-6 5'-O-(4,4'-dimethoxytrityl)-N²-isobutyryl-N¹,N²-bis(isobutyryloxy)ethylenedeoxyguanosine 

Downstream Products

• 1256294-82-2 N₂-isobutyryl-1,N₂-[1,2-di(isobutyryloxy)ethylene]-3',5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) 

Relevant academic research and scientific papers

Synthesis of oligodeoxynucleotides using fully protected Deoxynucleoside 3c-Phosphoramidite building blocks and base recognition of Oligodeoxynucleotides incorporating N3-Cyano-Ethylthymine

Oligodeoxynucleotide (ODN) synthesis, which avoids the formation of side products, is of great importance to biochemistry-based technology development. One side reaction of ODN synthesis is the cyanoethylation of the nucleobases. We suppressed this reaction by synthesizing ODNs using fully protected deoxynucleoside 3c-phosphoramidite building blocks, where the remaining reactive nucleobase residues were completely protected with acyl-, diacyl-, and acyl-oxyethylene-type groups. The detailed analysis of cyanoethylation at the nucleobase site showed that N3-protection of the thymine base efficiently suppressed the Michael addition of acrylonitrile. An ODN incorporating N3-cyanoethylthymine was synthesized using the phosphoramidite method, and primer extension reactions involving this ODN template were examined. As a result, the modified thymine produced has been proven to serve as a chain terminator.

Solid Phase Synthesis of Oligodeoxyribonucleotides Utilizing the Phenylthio Group as a Phosphate Protecting Group

Oligodeoxyribonucleotide synthesis utilizing the phenylthio group as a phosphate protecting group was applied to the solid phase method.The base residues of deoxyguanosine and deoxyadenosine were protected with bis(isobutyryloxy)ethylene (Bibe) and phthaloyl groups to avoid the base modfication and depurination, respectively.A key synthetic intermediate of N2-isobutyryl-N1,N2-bis(isobutyryloxy)ethylenedeoxyguanosine was prepared in high yield by four-step reaction from deoxyguanosine and used for preparation of the building blocks of deoxyguanosine required for the polymer support synthesis.Two kinds of polymer supports, i.e., 1 percent cross-linked polystyrene and controlled pore glass were chosen.The latter was employed for the synthesis of dodecadeoxyribonucleotides by using an automated DNA synthesizer.