199436-67-4

Upstream product

• 14204-31-0 2-(4-chlorophenylthio)isoindoline-1,3-dione 
• 649719-47-1 C₅₉H₅₇N₈O₁₄P 
• 40608-06-8 levulinic anhydride 
• 91592-66-4 N-benzoyl-3'-O-levulinoyl-2'-deoxy-β-D-cytidine 
• 93134-38-4 (2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-yl-4-oxopentanoate 
• 64325-78-6 N₆-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine 
• 67219-55-0 4-N-Benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine 
• 118352-75-3 Triethylammonium 6-N-benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)adenosine 3'-H-phosphonate 

Downstream Products

• 199436-72-1 4-Oxo-pentanoic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[[(2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-(4-chloro-phenylsulfanyl)-phosphoryloxymethyl]-tetrahydro-furan-3-yl ester 

Relevant academic research and scientific papers

The H-phosphonate approach to the synthesis of oligonucleotides and their phosphorothioate analogues in solution

A new approach to the synthesis of oligonucleotides and oligonucleotide phosphorothioates in solution is described; it is based on H-phosphonate coupling [with bis(2-chlorophenyl) phosphorochloridate 22 as the coupling agent] at -40 deg C, followed by in situ sulfur transfer involving either 2-(4-chlorophenylsulfanyl)isoindole-1,3(2H)-dione 23a or 4-[(2-cyanoethyl)sulfanyl]morpholine-3,5-dione 26. The yields of the coupling and sulfur transfer reactions are virtually quantitative and, following unblocking by previously reported procedures, very pure products (d[ApC], d[TpGpApC], d[TpGp(s)ApC], d[Gp(s)A] and d[Cp(s)Tp(s)Gp(s)A]) are obtained.

A new approach to oligonucleotide synthesis in solution

A new approach, based on the use of 3'-H-phosphonate building blocks, is described for the synthesis of oligonucleotides and their phosphorothioate analogues in solution.