189153-41-1

Upstream product

• 21090-30-2 3'-O-acetylthymidine 
• 50-89-5 thymidine 
• 189153-28-4 Thiophosphoric acid O-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester O'-(2-cyano-ethyl) ester S-pyridin-2-ylmethyl ester 
• 102987-83-7 5′-O-(4,4′-dimethoxytrityl)thymidine-3′-O-[2-cyanoethyl]phosphonate 
• 98796-51-1 5'-O-(4,4'-dimethoxytrityl)-2'-deoxythymidine-3'-O-[O-(2-cyanoethyl)-N,N'-diisopropylphosphoramidite] 
• 206061-72-5 5'-O-DMT-thymidine-3'-(2-picoline)thiophosphonate 
• 206061-69-0 2-picolylthiophosphoro-bis-triazolide 
• 2044-73-7 2-(sulfanylmethyl)pyridine 
• 4377-33-7 2-chloromethylpyridine 
• 931-19-1 2-methylpyridine N-oxide 
• 189153-35-3 5'-O-DMT-thymidine-3'-(2-picoline)thiophosphate 

Downstream Products

• 92127-24-7 C₄₁H₄₅N₄O₁₃PS 
• 118149-31-8 C₄₃H₄₇N₄O₁₄PS 

Relevant academic research and scientific papers

Synthesis of oligodeoxynucleoside phosphoromonothioates and phosphorodithioates by a phosphotriester method

A phosphotriester method for the synthesis of dithymidine phosphoromonothioates and phosphorodithioates with new S-protecting groups has been investigated. Four of the S-protecting groups possesed catalytic activity, however side reactions occurred during deprotection. The best S- protecting group was 4-chloro-2-nitrobenzyl which could be removed with a minimum of side reactions (0.3 %). The coupling reagent PyFNOP (14) gave protected dithymidine phosphoromonothioate in 96 % yield after 15 rain coupling. Furthermore PyFNOP chemoselectively activates oxygen in nucleoside phosphorodithioate monomers 9 and can be used for the synthesis of oligodeoxynucleoside phosphorodithioates with mixed base sequences.

A new strategy for the synthesis of phosphorothioates of 2′-deoxyriboligonucleotides

2-Picoline thiol, a new reagent, has been indigenously prepared and a new strategy has been followed for the sulphurization of phosphate bond in nucleotide monomer. The 2-picolylthiophosphorobis-(triazolide) has been prepared using phosphite triester approach and treated with protected nucleosides to get phosphorothioate synthons. The two dimers, d(GpT) and d(TpT) have been synthesised in very good yields using these synthons. The removal of 2-methylpyridyl group at the end of synthesis is achieved with 1,1,3,3-tetramethylguanidinium-4-nitrobenzaldoxime in dioxane-water.

Solution phase synthesis of dithymidine phosphorothioate by a phosphotriester method using new S-protecting groups

A phosphotriester method for the synthesis of dithymidine phosphorothioates with eight S-protecting groups has been investigated. Three of the S-protecting groups possesed catalytic activity, however side reactions occurred under deprotection. The best S-protecting group was 4- chloro-2-nitrobenzyl which could be removed with a minimum of side reactions (0.3 %). The coupling reagent PyFNOP (11) gave protected dithymidine phosphorothioate in 96 % yield after 15 min coupling.