31766-13-9

Basic information

• Product Name: 2',3'-Anhydroinosine
• Synonyms: 9-(2,3-Anhydro-β-D-ribofuranosyl)-1,9-dihydro-6H-purin-6-one;2',3'-Anhydroinosine
• CAS NO: 31766-13-9
• Molecular Formula: C10H10N4O4
• Molecular Weight: 250.2108
• Product Categories: Impurities;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Bases & Related Reagents;Heterocycles
• Mol File: 31766-13-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 712.4±60.0 °C(Predicted)
• Appearance: /
• Density: 2.23±0.1 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly, Heated)
• PKA: 8.92±0.70(Predicted)
• CAS DataBase Reference: 2',3'-Anhydroinosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-Anhydroinosine(31766-13-9)
• EPA Substance Registry System: 2',3'-Anhydroinosine(31766-13-9)

Safety Data

• Hazardous Substances Data: 31766-13-9(Hazardous Substances Data)

Usage

Uses

An impurity of the antiviral drug 2’3’Dideoxyinosine (D440950).

Upstream product

• 58-63-9 inosine 

Downstream Products

• 174467-01-7 9-[(2R,3S,4S,5R)-3-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-4-(5-nitro-pyridin-2-yldisulfanyl)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one 
• 183728-88-3 9-{(2R,3S,4R,5R)-3-Hydroxy-4-iodo-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1,9-dihydro-purin-6-one 
• 174467-02-8 9-<5-O-(monomethoxytrityl)-3-deoxy-3-S-(5-nitropyridyl-2-disulfanyl)-2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>hypoxanthine 
• 174466-93-4 9-<5-O-(monomethoxytrityl)-3-deoxy-3-thio-3-S,2-O-diacetyl-β-D-ribofuranosyl>hypoxanthine 

Relevant articles and documents

Nucleic Acid Related Compounds. 88. Efficient Conversions of Ribonucleosides into Their 2',3'-Anhydro, 2'(and 3')-Deoxy, 2',3'-Didehydro-2',3'-dideoxy, and 2',3'-Dideoxynucleoside Analogues

Treatment of purine, pyrimidine, and modified purine (antibiotic) ribonucleosides with 2-acetoxy-2-methylpropanoyl (α-acetoxyisobutyryl) bromide in acetonitrile gave mixtures of 2',3'-bromohydrin acetates with different O5' substituents.Significant amounts of 5'-unprotected (hydroxyl) bromo acetates were obtained in some cases, and formation of 2',3'-O-isopropylidene derivatives as minor byproducts was detected for the first time.Acid-catalyzed nucleophilic displacement of chloride by bromide occurred with 2-amino-6-chloropurine riboside, but no substitution of fluoride by bromide was detected with 6-amino- 2-fluoropurine riboside.Treatment of the trans bromo acetate mixtures obtained from purine-type nucleosides with Dowex 1 x 2 (OH(-)) in methanol gave the 2',3'-anhydro (ribo epoxide) compounds.Radical-mediated hydrogenolytic debromination and deprotection gave 2'- and 3'-deoxynucleosides.Treatment of the bromo acetate mixtures with zinc-copper couple or acetic acid-activated zinc effected reductive elimination, and deprotection gave 2',3'-didehydro-2',3'-dideoxy compounds which were hydrogenated to give 2',3'-dideoxynucleosides.A number of these analogues have potent inhibitory activity against AIDS and hepatitis B viruses.New 13C NMR data for several types of unsaturated-sugar nucleosides are tabulated.These procedures are directly applicable for the preparation of L-didehydro-dideoxy and L-dideoxy nucleoside analogues.