184773-07-7

Upstream product

• 189153-27-3 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 S-(4-chloro-2-nitro-benzyl) ester O'-(2-cyano-ethyl) 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] 
• 21090-30-2 3'-O-acetylthymidine 

Downstream Products

• 118149-31-8 C₄₃H₄₇N₄O₁₄PS 

Relevant academic research and scientific papers

Solution phase synthesis of dithymidine phosphorodithioate using new S- protecting groups in combination with a chemoselective coupling reagent (PyNOP)

A method for the synthesis of O-thymidin-3'-yl S-alkyl dithiophosphate monomers 1 with different S-protecting groups has been developed. These have been used for solution phase synthesis of dithymidine phosphorodithioate by a new phosphotriester method. C

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.

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.