3969-27-5

Basic information

• Product Name: 8-methoxy-9-pentofuranosyl-9H-purin-6-amine
• CAS NO: 3969-27-5
• Molecular Formula: C₁₁H₁₅N₅O₅
• Molecular Weight: 297.2673
• Mol File: 3969-27-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 661.7°C at 760 mmHg
• Flash Point: 354°C
• Density: 1.98g/cm³
• Vapor Pressure: 2.08E-18mmHg at 25°C
• Refractive Index: 1.829
• CAS DataBase Reference: 8-methoxy-9-pentofuranosyl-9H-purin-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-methoxy-9-pentofuranosyl-9H-purin-6-amine(3969-27-5)
• EPA Substance Registry System: 8-methoxy-9-pentofuranosyl-9H-purin-6-amine(3969-27-5)

Safety Data

• Hazardous Substances Data: 3969-27-5(Hazardous Substances Data)

Upstream product

• 124-41-4 sodium methylate 
• 2946-39-6 8-bromoadenosine 
• 67-56-1 methanol 
• 23205-66-5 O^2'_,O3'_,O5'5'-triacetyl-8-fluoro-adenosine 
• 58-61-7 adenosine 

Relevant articles and documents

Cyclic dinucleotide analogues, pharmaceutical composition of analogues and applications of analogues and pharmaceutical composition

The invention discloses cyclic dinucleotide analogues, a pharmaceutical composition of the analogues and applications of the analogues and the pharmaceutical composition. The cyclic dinucleotide analogs (I), an isomer, prodrug, stable isotope derivative or pharmaceutically acceptable salt of the analogs have a structure shown in the specification. The cyclic dinucleotide analogs provided by the invention can be used as regulators of stimulator of interferon genes (STIG) and related signaling pathways, and can effectively treat and/or alleviate multiple types of diseases, including but not limited to malignant tumors, inflammation, autoimmune diseases and infectious diseases; and in addition, the STING regulators can also be used as vaccine adjuvants.

Kinetics and mechanism of the defluorination of 8-fluoropurine nucleosides in basic and acidic media

For investigating the stability of C(8)-fluorine bond in 8-fluoropurine nucleosides some protected 8-fluoroguanosine, 8-fluoroinosine and 8-fluoroadenosine derivatives were prepared by direct fluorination of acetyl-protected purine nucleosides with elemental fluorine in solvents such as chloroform, acetonitrile and nitromethane. Fluorination reactions conducted in chloroform medium gave better yields of 8-fluoropurines. The fluorination yields were slightly lower when acetonitrile or nitromethane was used as solvent, but the product purification was found to be much easier. When the synthesized, protected fluoronucleosides were subjected to standard basic (NH3 in methanol or 2-propanol) and acidic (HCl in methanol) deprotection conditions relevant to nucleoside chemistry, an efficient defluorination reaction took place. The kinetics of these defluorination reactions were conveniently followed, under pseudo-first-order reaction conditions, using 19F NMR spectroscopy. 1H NMR, LC-MS and mass spectroscopy identified the products of the kinetic reaction mixtures. The defluorination reaction rate constants (kobs) in basic media depended upon the electron density at C(8) while the kobs data in acidic medium were determined by the pKa of N7. An addition-elimination based mechanism (SNAr) has been proposed for the defluorination reactions of these 8-fluoropurine nucleosides.