42867-68-5

Basic information

• Product Name: 2',3'-Dideoxy-2',3'-didehydroinosine
• Synonyms: 9-[(2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-3h-purin-6-one;2',3'-DIDEHYDRO-2',3'-DIDEOXYINOSINE;2',3'-Dideoxy-2',3'-didehydroinosine;2'',3''-DIDEOXY-2'',3''-DIDEHYDRO- INOSINE [D4I];2'',3''-DIDEOXY-2'',3''-DIDEHYDRO- INOSINE SODIUM [D4I SODIUM];9-[(2R,5S)-5-methylol-2,5-dihydrofuran-2-yl]-3H-purin-6-one;9-((2R,5S)-5-(HydroxyMethyl)-2,5-dihydrofuran-2-yl)-3H-purin-6(9H)-one;9-((2R,5S)-5-(HydroxyMethyl)-2,5-dihydrofuran-2-yl)-3H-purin-6(9H)-one sodium
• CAS NO: 42867-68-5
• Molecular Formula: C₁₀H₁₀N₄O₃
• Molecular Weight: 234.2114
• EINECS: 1308068-626-2
• Mol File: 42867-68-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 604.8°C at 760 mmHg
• Flash Point: 319.6 °C
• Appearance: /
• Density: 1.74 g/cm³
• Storage Temp.: 2-8°C
• PKA: 8.92±0.70(Predicted)
• CAS DataBase Reference: 2',3'-Dideoxy-2',3'-didehydroinosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-Dideoxy-2',3'-didehydroinosine(42867-68-5)
• EPA Substance Registry System: 2',3'-Dideoxy-2',3'-didehydroinosine(42867-68-5)

Safety Data

• Hazardous Substances Data: 42867-68-5(Hazardous Substances Data)

Usage

Uses

2’,3’-Didehydrodidanosine (Didanosine EP Impurity F) is an impurity of Didanosine (D440950), which used as an antiviral agent. Classed as an anti-retroviral drug used in the treatment of HIV in ART therapy, it also may increase acetaminophen related hepatotoxicity by enhancing mitochrondrial dysfunction (2).

Upstream product

• 130676-57-2 1-(5-O-Acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)hypoxanthine 
• 58-63-9 inosine 
• 142504-05-0 2',3'-didehydro-5'-O-(2,5,5-trimethyl-1,3-dioxolan-4-on-2-yl)-2',3'-dideoxyinosine 
• 810694-82-7 2',3'-bis-O-[(methylthio)thiocarbonyl]inosine 
• 119794-35-3 5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<<(β-cyanoethyl)thio>thiocarbonyl>inosine 
• 119794-36-4 D-2',3'-O-thiocarbonylene-5'-O-tert-butyldimethylsilyl inosine 
• 119794-34-2 5’-O-tert-butyldimethylsilyl-inosine 
• 58-63-9 Inosine 
• 125790-82-1 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)-1,9-dihydro-6H-purine-6-one 
• 65870-99-7 2',3'-O-(1-methoxyethylidene)inosine 
• 142544-61-4 2-Acetoxy-2-methyl-propionic acid (2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-2,5-dihydro-furan-2-ylmethyl ester 
• 119818-51-8 5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxyinosine 

Downstream Products

• 69655-05-6 Dideoxyinosine 

Relevant articles and documents

Synthesis of novel 2′,3′-Didehydro-2′,3′- dideoxyinosine phosphoramidate prodrugs and evaluation of their anticancer activity

An efficient synthesis of 4-chlorophenyl N-alkyl phosphoramidates of 2 ′,3 ′-didehydro-2 ′,3 ′-dideoxyinosine employing 4-chlorophenyl phosphoroditetrazolide as a phosphorylating agent is reported. Improved method for the synthesis of 2 ′,3 ′-didehydro-2

A NOVEL PROCESS FOR THE PREPARATION OF DIDANOSINE USING NOVEL INTERMEDIATES

The present invention relates to novel crystalline alkali metal and alkaline earth metal salts of 2',3'-dideoxy-2',3'-didehydroinosine. The present invention also provides a novel process for preparation of didanosine in high yield and purity using novel intermediates. Thus, for example, 5'-O-acetyl-2',3'-dideoxy-2',3'-didehydroinosine is reacted with monomethyl amine to give 2',3'-dideoxy-2',3'-didehydro inosine, which is then reacted with sodium hydroxide and crystallized to give crystalline 2',3'-dideoxy-2',3'-didehydroinosine sodium salt. 2',3'-Dideoxy-2',3'-didehydroinosine sodium salt is hydrogenated using raney nickel catalyst in aqueous medium and then neutralized with hydrochloric acid to yield didanosine.

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.