118149-31-8

Basic information

• Product Name: 5'-O-dimethoxytritylthimidine-3'-O-(5'-O-thymidylyl-3'-O-acetyl)phosphorothioate
• Synonyms: 5'-O-dimethoxytritylthimidine-3'-O-(5'-O-thymidylyl-3'-O-acetyl)phosphorothioate
• CAS NO: 118149-31-8
• Molecular Weight: 906.904
• Mol File: 118149-31-8.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 5'-O-dimethoxytritylthimidine-3'-O-(5'-O-thymidylyl-3'-O-acetyl)phosphorothioate(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-dimethoxytritylthimidine-3'-O-(5'-O-thymidylyl-3'-O-acetyl)phosphorothioate(118149-31-8)
• EPA Substance Registry System: 5'-O-dimethoxytritylthimidine-3'-O-(5'-O-thymidylyl-3'-O-acetyl)phosphorothioate(118149-31-8)

Safety Data

• Hazardous Substances Data: 118149-31-8(Hazardous Substances Data)

Upstream product

• 50-89-5 thymidine 
• 1196870-93-5 5'-O-dimethoxytritylthymidine-3'-O-(2-oxo-1,3,2-dithiaphospholane) 
• 21090-30-2 3'-O-acetylthymidine 
• 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 
• 98796-51-1 5'-O-(4,4'-dimethoxytrityl)-2'-deoxythymidine-3'-O-[O-(2-cyanoethyl)-N,N'-diisopropylphosphoramidite] 
• 189153-41-1 C₄₉H₅₂N₅O₁₄PS 
• 184773-07-7 C₅₀H₅₁ClN₅O₁₆PS 
• 129789-72-6 C₅₀H₅₁Cl₂N₄O₁₄PS 
• 189153-43-3 C₄₉H₅₂N₅O₁₅PS 
• 184773-08-8 C₄₈H₅₃N₆O₁₄PS 
• 189153-40-0 C₅₀H₅₂N₅O₁₆PS 
• 189153-44-4 C₄₉H₅₅N₆O₁₅PS 
• 189153-42-2 C₄₉H₅₁ClN₅O₁₄PS 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 

Downstream Products

• 92127-24-7 C₄₁H₄₅N₄O₁₃PS 

Relevant articles and documents

Chemoselective synthesis of dithymidine phosphorothioate in solution using O-protected thiophosphate monomers

Diastereomerically pure O-protected thymine monothioate nucleotide (I) is efficiently coupled to protected thymidine (II) in a chemoselective, but not stereoselective manner, to give dithymidine phosphorothioates (III).

Studies of asymmetric induction in the synthesis of dinucleoside phosphorothioates from 2-oxo-1,3,2-dithiaphospholane nucleoside derivatives

The nucleoside derivatives, containing at 3'-O or 5'-O-position 2-oxo-1,3,2-dithiaphospholane function were found to react in the presence of DBU with a hydroxyl group of appropriately protected nucleosides to yield, after deprotection, dinucleoside phosphorothioates in moderate yields. An asymmetric induction connected with the formation of new chiral phosphorothioate center has been examined.

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.