189153-41-1

Basic information

• Product Name: C₄₉H₅₂N₅O₁₄PS
• Synonyms: C₄₉H₅₂N₅O₁₄PS
• CAS NO: 189153-41-1
• Molecular Weight: 998.017
• Mol File: 189153-41-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₄₉H₅₂N₅O₁₄PS(CAS DataBase Reference)
• NIST Chemistry Reference: C₄₉H₅₂N₅O₁₄PS(189153-41-1)
• EPA Substance Registry System: C₄₉H₅₂N₅O₁₄PS(189153-41-1)

Safety Data

• Hazardous Substances Data: 189153-41-1(Hazardous Substances Data)

Upstream product

• 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] 
• 50-89-5 thymidine 
• 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 
• 21090-30-2 3'-O-acetylthymidine 
• 189153-35-3 5'-O-DMT-thymidine-3'-(2-picoline)thiophosphate 

Downstream Products

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

Relevant articles and documents

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.

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.