189307-27-5

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 177569-52-7 5'(R)-C-allyl-3'-O-(tert-butyldimethylsilyl)thymidine 
• 50-89-5 thymidine 
• 40733-26-4 3',5'-O-di(tert-butyldimethylsilyl)thymidine 
• 131118-61-1 3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde 

Downstream Products

• 208839-29-6 5'(R)-C-allyl-5'-O-(4,4'-dimethoxytrityl)thymidine 
• 189307-28-6 1-[(2R,4S,5R)-5-{(R)-1-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-4-hydroxy-butyl}-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 189307-30-0 5'(R)-C-acetoxypropyl-5'-O-(4,4-dimethoxytrityl)thymidine 

Relevant academic research and scientific papers

Synthesis of 5'-C-branched thymidines and conversion to phosphoramidites

Thymidine was converted to its 5'-epoxy derivative, which was reacted with nucleophiles to give 5'-C-aminomethyl-, 5'-C-bromomethyl-, 5'-C- cyanomethyl, and 5'-C-methoxymethylthymidine derivatives with defined stereochemistry. 5'-C-ally-, 5'-C-hydroxymethyl-, 5'-C-hydroxypropyl-, and 5'-C-(imidazole-4-acetamido)methylthymidine derivatives were also prepared. The 5'-C-branched thymidines were converted to the corresponding phosphoramidites.

5'-C-Branched thymidines: Synthesis, stereochemistry, and incorporation into oligodeoxynucleotides

Thymidine was converted to its 5'(S)-epoxy derivative, which reacted with nucleophiles to give 5'(S)-C-aminomethyl-, 5'(S)-C-azidomethyl, 5'(S)-C-cyanomethyl-, and 5'(S)-C-methoxymethyl-thymidine with defined stereochemistry. 5'-C-Allyl- and 5'-C-nitromethylthymidines were prepared from an aldehyde derivative. Stereochemistry of 5'-C-branched thymidines was assigned with the help of NOE experiments. Four 5'-C-branched thymidines were incorporated into oligodeoxynucleotides.