137147-01-4

Upstream product

• 20290-92-0 1-<2',3',5'-Tri-O-benzoyl-α-L-arabinofuranosyl>thymine 
• 87-72-9 L-(+)-arabinose 
• 7791-71-1 1-(5-O-trityl-2-deoxy-β-D-lyxofuranosyl)thymine 
• 16033-24-2 1-<α-L-Arabinofuranosyl>thymine 
• 3795-68-4 methyl α-L-arabinofuranoside 
• 189074-35-9 1-O-Acetyl-2,3,5-tri-O-benzoyl-α/β-L-arabinofuranoside 
• 137147-00-3 1-<2'-O-Phenoxythiocarbonyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-L-arabinofuranosyl>thymine 
• 137146-99-7 1-<3',5'-O-(1,1,3,3-Tetraisopropyldisiloxane-1,3-diyl)-α-L-arabinofuranosyl>thymine 
• 137174-38-0 5-methyl-1-((6aR,8R,9aR)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione 
• 42793-97-5 2,3,5-tri-O-benzoyl-1-O-methyl-α-L-arabinofuranose 
• 131682-41-2 1-[(2R,4R,5S)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4-dione 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 137147-02-5 1-(3'-Azido-2',3'-dideoxy-5'-O-triphenylmethyl-α-L-threo-pentofuranosyl)thymine 
• 132970-02-6 1-(3'-Azido-2',3'-dideoxy-α-L-threo-pentofuranosyl)thymine 

Relevant academic research and scientific papers

Labelling compounds for the simple synthesis of 3'-(18f)fluoro-3'-deoxy thymidine and a method for the production thereof

The application relates to compounds that are suitable as labelable precursors for synthesis of 3′-[18F]fluoro-3′-deoxythymidine and that have formula (1), 1in which R denotes triphenylmethyl, triphenylmethyl substituted in the phenyl group, trialkylmethyl, triphenylsilyl, triphenylsilyl substituted in the phenyl group, or trialkylsilyl, R′ denotes R1—SO2, where R1 is an unsubstituted or substituted C1 to C5 alkyl or an unsubstituted or substituted phenyl, and R″ denotes C2 to C10 alkyloxycarbonyl, with the exception of 3-N-Boc-1-(3-O-nosyl-5-O-trityl-2-deoxy-β-D-lyxofuranosyl)thymine. The application also relates to a method for preparation of these compounds and to the use of the same for synthesis of 3′-[18F]fluoro-3′-deoxythymidine.

Synthesis of 1-(3'-azido-2',3'-dideoxy-α-L-threo-pentofuranosyl)thymine as a potential anti-HIV agent

Starting from methyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranoside, a multistep synthesis of the C-4' epimer of AZT is described. Glycosylation of silylated thymine with 2,3,5-tri-O-benzoyl-L-arabinofuranosyl acetate (5) affords the α-nucleoside 7 after debenzoylation. Deoxygenation at C-2' of the selectively protected 8, followed by displacement of a 3'-methanesulfonyl group by lithium azide leads to the title compound which did not exhibit antiviral activity against HIV-1.