125178-07-6

Basic information

• Product Name: 2'-deoxyribofuranosyl-1-deazapurine
• Synonyms: 2'-deoxyribofuranosyl-1-deazapurine
• CAS NO: 125178-07-6
• Molecular Formula: C₁₁H₁₃N₃O₃
• Molecular Weight: 235.23922
• Mol File: 125178-07-6.mol

Chemical Properties

• Boiling Point: 528.8°Cat760mmHg
• Flash Point: 273.6°C
• Appearance: /
• Density: 1.61g/cm³
• CAS DataBase Reference: 2'-deoxyribofuranosyl-1-deazapurine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-deoxyribofuranosyl-1-deazapurine(125178-07-6)
• EPA Substance Registry System: 2'-deoxyribofuranosyl-1-deazapurine(125178-07-6)

Safety Data

• Hazardous Substances Data: 125178-07-6(Hazardous Substances Data)

Upstream product

• 159944-82-8 5,7-dichloro-3-(2-deoxy-β-D-erythro-pentofuranosyl)-3H-imidazo[4,5-b]pyridine 
• 951-78-0 2'-deoxyuridine 
• 273-21-2 3H-imidazo[4,5-b]pyridine 
• 3601-89-6 Hoffer's chlorosugar 
• 24485-01-6 5,7-dichloro-3H-imidazo<4,5-b>pyrimidine 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 

Downstream Products

• 36792-88-8 2-deoxy-D-ribose 
• 273-21-2 1H-Imidazo[4,5-b]pyridine 

Relevant articles and documents

SYNTHESIS OF 2-DEOXY-β-D-RIBONUCLEOSIDES AND2,3-DIDEOXY.β-D-PENTOFURANOSIDES ON IMMOBILIZED BACTERIAL CELLS

Alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli catalyze the transfer of 2-deoxy-D-ribofuranosyl moiety of 2'-deoxyuridine to purine and pyrimidine bases as well as their aza and deaza analogs.All experiments invariably gave β-anomers; in most cases, the reaction was regiospecific, affording N9-isomers in the purine and N1-isomers in the pyrimidine series.Also a 2,3-dideoxynucleoside can serve as donor of the glycosyl moiety.The acceptor activity of purine bases depends only little on substitution, the only condition being the presence of N7-nitrogen atom.On the other hand, in the pyrimidine series the activity is limited to only a narrow choice of mostly short 5-alkyl and 5-halogeno uracil derivatives.Heterocyclic bases containing amino groups are deaminated; this can be avoided by conversion of the base to the corresponding N-dimethylaminomethylene derivative which is then ammonolyzed.The method was verified by isolation of 9-(2-deoxy-β-D-ribofuranosyl) derivatives of adenine, guanine, 2-chloroadenine, 6-methylpurine, 8-azaadenine, 8-azaguanine, 1-deazaadenine, 3-deazaadenine, 1-(2-deoxy-β-D-ribofuranosyl) derivatives of 5-ethyluracil, 5-fluorouracil, and 9-(2,3-deoxy-β-D-pentofuranosyl)hypoxanthine, 9-(2,3-deoxy-β-D-pentofuranosyl)-6-methylpurine, and other nucleosides.

Synthesis of 2'-deoxyribonucleoside derivatives of 1-deazapurine

5,7-Dichloro-3H-imidazo[4,5-b]pyridine (4) is a versatile base which can be coupled with a variety of sugar moieties and transformed in a series of 7- alkyl(aryl)amino-derivatives by reacting with the corresponding amines. In this paper synthesis, structure elucidation and ADA inhibitory activity of 2'-deoxyribonucleoside derivatives of N6-substituted 1-deazaapurines are described.

Synthesis of 6-substituted 1-deazapurine 2'-deoxyribonucleosides

The synthesis of 6-substituted 1-deazapurine 2'-deoxyribonucleosides is described. Glycosylation of the 1-deazapurine (imidazo[4,5-b]pyridine) anions with the α-D-halogenose 5 gives stereoselectively N7- and N9-regioisomers. 1H-NMR NOE and 13C-NMR spectroscopy are used for unambiguous assignment of isomers, and 15N-NMR chemical shifts are correlated with σ(para) Hammett constants and point charges.