258502-38-4

Upstream product

• 194596-15-1 5-(2-chloroethyl) 1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-ribofuranosyl]-4-(1H-1,2,4-triazol-1-yl)pyrimidin-1(1H)-one 
• 90301-69-2 5-(2-chloroethyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-1H,3H-pyrimidine-2,4-dione 

Downstream Products

• 258502-42-0 7-amino-3-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-ribofuranosyl]-3,5,6,7-tetrahydro-2H-pyrrolo[2,3-d]pyrimidin-2-one 
• 303766-15-6 2-acetyl-6-(3,5-di-O-p-toluoyl-β-D-2-deoxyribofuranosyl)-3,4-dihydro-8H-pyrimido[4,5-c]pyridazin-7-one 

Relevant academic research and scientific papers

The syntheses of pyrimido-pyridazinone and pyrrolidino-pyrimidinone 2'-deoxynucleoside derivatives

Nucleosides that have ambivalent tautomeric properties have value in a variety of nucleic-acid hybridisation applications and as mutagenic agents. We describe here synthetic studies directed to stable derivatives based on N4-aminocytosine. Treatment of the 5-(chloroethyl)-4-(triazol-1-yl)pyrimidine-nucleoside derivative 1 with benzylhydrazine leads to the formation of the 6,6-bicyclic pyrimido-pyridazin-7-one 6, in addition to the 5,6-bicyclic derivative 7. The 6,6-bicyclic benzyl derivative 6 was converted to its 5'-triphosphate for studies with DNA polymerases. Reaction of the triazole 1 with hydrazine, followed by acetylation, led to the desired acetylated 6,6-bicyclic derivative 12. However, the latter compound undergoes acyl migration followed by ring contraction to the 5,6-bicyclic compound 13 on treatment with base.

The synthesis of bicyclic N4-amino-2'-deoxycytidine derivatives

Nucleosides which have ambivalent tautomeric properties have value in a variety of nucleic acid hybridization applications, and as mutagenic agents. We describe here synthetic studies directed to stable derivatives of this kind of nucleoside based on Nsu