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

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

Downstream Products

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

Relevant articles and documents

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.