272116-45-7

Upstream product

• 108-98-5 thiophenol 
• 75106-39-7 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(5-acetoxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 951-78-0 2'-deoxyuridine 
• 5116-24-5 2'-deoxy-5-(hydroxymethyl)uridine 

Downstream Products

• 272116-56-0 5'-O-(4,4'-dimethoxytrityl)-5-(phenylthiomethyl)-2'-deoxyuridine 
• 70465-55-3 5-(aminomethyl)-2'-deoxyuridine 
• 272116-47-9 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-5-phenylsulfanylmethyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 
• 622402-63-5 Acetic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-5-phenylsulfanylmethyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 111476-41-6 Acetic acid (2R,3S,5R)-5-(2,4-dioxo-5-phenylsulfanylmethyl-3,4-dihydro-2H-pyrimidin-1-yl)-2-methanesulfonyloxymethyl-tetrahydro-furan-3-yl ester 
• 111476-36-9 3'-O-acetyl-2',5'-dideoxy-5'-iodo-5-phenylthiomethyluridine 
• 111476-35-8 3'-O-acetyl-5-(phenylthiomethyl)-2'-deoxyuridine 
• 272116-46-8 5-(phenylthiomethyl)-2'-deoxyuridine 

Relevant academic research and scientific papers

Synthesis and UV photolysis of oligodeoxynucleotides that contain 5-(phenylthiomethyl)-2'-deoxyuridine: a specific photolabile precursor of 5-(2'-deoxyuridilyl)methyl radical.

[formula: see text] The title exocyclic radical (2) is generated via photochemical cleavage of 5-(phenylthiomethyl)-2'-deoxyuridine (8). The latter thionucleoside (8) was successfully incorporated into DNA oligomers by automated DNA synthesis using phosphoramidite chemistry. UV exposure of 8 containing oligonucleotides under (an)aerobic conditions gives rise to specific base lesions. The photoproducts have been isolated and further characterized on the basis of detailed NMR and mass spectrometric analyses.

SYNTHESIS OF 6,5'-cyclo-2',5'-DIDEOXYPYRIMIDINE NUCLEOSIDES ( NUCLEOSIDES AND NUCLEOTIDES. LXXII )

6,5'-cyclo-2',5'-dideoxyuridine and 6,5'-cyclo-5'-deoxythymidine, pyrimidine deoxynucleosides fixed in the anti conformation were synthesized.The key intermediate, 3'-O-acetyl-5-chloro-2',5'-dideoxy-5'-iodouridine ( 12 ), prepared from 2'-deoxyuridine, was cyclized by treatment with tributyltin hydride to the 6,5'-cyclo derivative ( 13 ), then dehydrochlorinated to furnish, after de-O-acetylation, 6,5'-cyclo-2',5'dideoxyuridine ( 14 ).For the synthesis of 6,5'-cyclothymidine, 3'-O-acetyl-2',5'-dideoxy-5'-iodo-5-phenylthiomethyluridine ( 22 ) was prepared from 2'-deoxyuridine and this compound was cyclized by treatment with tributyltin hydride to yield, after de-O-acetylation 6,5'-cyclo-5'-deoxythymidine ( 24 ).Keywords - cyclonucleoside; C-cyclouridine; 6,5'-cyclo-2',5'-dideoxyuridine; 6,5'-cyclo-5'deoxythymidine; 5-bromo-6,5'-cyclo-2',5'-dideoxyuridine; radical cyclization; tributyltin hydride; NMR; CD