76859-58-0

Upstream product

• 772-79-2 4-chlorophenylphosphorodichloridate 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 65062-61-5 4-chlorophenyl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl phosphate triethylammonium salt 
• 67221-57-2 5'-O-(dimethoxytrityl)thymidine 3'-(p-chlorphenylcyanoethyl phosphate) 
• 93403-76-0 5'-O-(dimethoxytrityl)thymidine 3'-(p-chlorophenyl phosphoromonochloridate) 
• 21090-30-2 3'-O-acetylthymidine 
• 93403-69-1 C₇₄H₇₀Cl₂N₄O₁₉P₂ 
• 65062-60-4 4-chlorophenyl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl phosphate 
• 93403-66-8 C₄₆H₄₆ClN₂O₁₂PS 
• 93403-75-9 5'-O-(dimethoxytrityl)thymidine 3'-(p-chlorophenyl phosphoro-3-nitro-1,2,4-triazolide) 
• 93403-74-8 5'-O-(dimethoxytrityl)thymidine 3'-(p-chlorophenyl phosphorotetrazolide) 
• 93403-73-7 5'-O-(dimethoxytrityl)thymidine 3'-(p-chlorophenyl phosphoro-1,2,4-triazolide) 
• 93403-72-6 5'-O-(dimethoxytrityl)thymidine 3'-(p-chlorophenyl phosphorimidazolide) 
• 773-64-8 2-mesitylenesulphonyl chloride 

Downstream Products

• 68892-37-5 C₄₇H₄₈ClN₄O₁₄P 
• 7177-84-6 DMTrOTpT 

Relevant academic research and scientific papers

Comparison of rates of phosphotriester formation and sulphonation by coupling agents in oligodeoxyribonucleotide synthesis by the phosphotriester method

Rates of phosphotriester bond formation and amounts of sulphonation are compared for three popular coupling agents used in oligodeoxyribonucleotide synthesis by the phosphotriester approach.

31P NMR Study of the Mechanism of Activation and Coupling Reactions in the Synthesis of Oligodeoxyribonucleotides by the Phosphotriester Method

The phosphotriester method provides a rapid and convenient procedure for synthesizing oligonucleotides.The mechanism has been revealed and intermediates have been identified by 31P NMR methodology.It was found that reaction of a 5'-protected nucleoside 3'-(p-chlorophenyl phosphate) with mesitylenesulfonyl chloride (MSCl) or 1-(mesitylyl-2-sulfonyl)-3-nitro-1,2,4-triazole (MSNT) in anhydrous pyridine yields only two products within 5 min, the sulfonic acid-phosphate mixed anhydride 2 and the (3'-3') symmetrical pyrophosphate tetraester 3 which can be isolated as a mixture.Reaction of 2 and 3 with 3'-O-acetylthymidine yields the phosphotriester dimer NpTOAc.The reaction rate and yield of dimers are closely dependent on the presence of catalysts.The reaction finished within minutes when tetrazole or 3-nitro-1,2,4-triazole was used.On the contrary, the reaction completed in hours when imidazole or 1,2,4-triazole was used as catalysts.The possible mechanisms are explored and discussed in detail.