70465-55-3

Upstream product

• 59090-48-1 5-(azidomethyl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 
• 272116-46-8 5-(phenylthiomethyl)-2'-deoxyuridine 
• 244631-66-1 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-2'-deoxy-N³-pivaloyloxymethyluridine 
• 5116-24-5 2'-deoxy-5-(hydroxymethyl)uridine 
• 58589-18-7 3',5'-di-O-acetyl-5-bromomethyl-2'-deoxyuridine 
• 72274-20-5 3′,5′-di-O-acetyl-5-azidomethyl-2′-deoxyuridine 
• 272116-45-7 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(2,4-dioxo-5-phenylsulfanylmethyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 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 
• 629642-57-5 3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-methoxyacetyl-β-D-glucopyranosyl)oxymethyluridine 
• 629642-42-8 2'-deoxy-5-(2,3,4,6-tetra-O-methoxyacetyl-β-D-glucopyranosyl)oxymethyluridine 
• 629642-48-4 3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(β-D-glucopyranosyl)oxymethyluridine 
• 629642-40-6 2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxymethyluridine 
• 354581-65-0 3',5'-bis(O-tert-butyl-dimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxymethyluridine 

Relevant academic research and scientific papers

Reinvestigation into the synthesis of oligonucleotides containing 5-(β-D-glucopyranosyloxymethyl)-2′-deoxyuridine

A reinvestigation into the synthesis of oligonucleotides containing 5-(β-D-glucopyranosyloxymethyl)-2′-deoxyuridine revealed that existing procedures for the preparation of these DNA fragments suffered from decomposition at the final deprotection step. Th

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 a new analog of thymidine for in vivo non-radioactive labeling of DNA

The introduction of 6-(p-bromobenzoylamino)caproyl radical in the methyl group of 2'-O-deoxythymidine is described. In vivo incorporation of this nucleoside to DNA was determined using a monoclonal antibody that recognized the radical.

Synthesis and Biological Activities of 5-(Hydroxymethyl, azidomethyl, or aminomethyl)-2'-deoxyuridine and Related 5'-Substituted Analogues

The synthesis of 5-(azidomethyl)-2'-deoxyuridine (10) has been accomplished by two independent methods.The first involved tosylation of 5-(hydroxymethyl)-2'-deoxyuridine (1) to furnish a mixture of two mono- and a ditosyl nucleosides which were converted into the corresponding 5-(azidomethyl) (10), 5-(azidomethyl)-5'-azido (14), and 5-(hydroxymethyl)-5'-azido (15) derivatives of 2'-deoxyuridine.The second method was more selective and required the formation of the intermediate 5-(bromomethyl)-3',5'-di-O-acetyl-2'-deoxyuridine (8), followed by displacement of the bromo group by lithium azide and deacetylation.Catalytic hydrogenation of the azides 9, 10, 14, and 15 gave the corresponding amines 16, 2, 6, and 7, repectively.Compounds 1, 2, 10, and 16 inhibited the growth of murine Sarcoma 180 and L1210 in culture, and the activity of 2 was prevented by 2'-deoxypyrimidine nucleosides by not by purine nucleosides.The replication of herpes simplex virus type 1 (HSV-1) was strongly inhibited only by 1 and 10.Studies on the binding of the various thymidine analogues to HSV-1 encoded pyrimidine deoxyribonucleoside kinase indicate that 1 and 10 have good affinity for the enzyme.