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

Used in Antiviral Applications:
2',3'-Dideoxy-2',3'-didehydroinosine is used as an impurity in the antiviral agent Didanosine, which is employed in the treatment of HIV as part of ART (Antiretroviral Therapy). Its presence in Didanosine may contribute to the overall efficacy of the drug in combating the virus.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2',3'-Dideoxy-2',3'-didehydroinosine is used as a reference compound for the development and quality control of Didanosine. Understanding the properties and effects of this impurity can help in optimizing the manufacturing process and ensuring the safety and efficacy of the final drug product.

Upstream product

• 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 
• 130676-57-2 1-(5-O-Acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)hypoxanthine 
• 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.

Synthesis of 2′,3′-dideoxyinosine via radical deoxygenation

A synthetic method for 2′,3′-dideoxyinosine (ddI) from inosine was established via radical deoxygenation of N1,5′-O-diprotected-2′, 3′-bis-S-methyl dithiocarbonate of inosine derivatives. The radical deoxygenation proceeded smoothly to give the desired dideoxy compounds in good yields using 1-ethylpiperidinium hypophosphite and triethylborane. Benzyl or p-methoxybenzyl protection of inosine at the N1, 5′-O-positions were effective for the ddI synthesis. Copyright Taylor & Francis Group, LLC.

INOSINE DERIVATIVE AND PROCESS FOR PRODUCING THE SAME

The present invention provides a method for producing an inosine derivative represented by the following general formula (1) including the steps of subjecting an inosine derivative of general formula (3) to dithiocarbonylation and carrying out radical reduction of the obtained compound. According to the present invention there can be produced compounds useful as anti-AIDS drugs on industrial scale. wherein R1 may be the same or different and are each benzyl group, benzhydryl group or trityl group, each of which may have a substituent in general formulas (1) and (3).

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.

An efficient and general synthesis of 5'-esters of 2',3'-didehydro-2',3'-dideoxynucleosides: A facile opening of 2',3'-orthoacetates of ribonucleosides followed by reductive elimination of the halogenoacetates

A three-step reaction sequence from a ribonucleoside to give the corresponding 5'-O-acyl-2',3'-didehydro-2',3'-dideoxynucleoside is described. The key intermediate is the bromoacetate, made by reaction of the 2',3'-methoxyethylidine nucleoside with acetyl bromide. Reductive elimination of the bromoacetate using a zinc-copper couple furnishes the desired compounds in good overall yield.

Stereoselective glycosylation of hetercyclic bases

A method of preparation of 2',3'-dideoxy and 2',3'-dideoxy-2',3'-didehydronucleosides that includes the step of condensing a 1-O-activated-2-(aromatic or aliphatic)-selenenyl-5-O-protected ribose with a protected heterocyclic base in the presence of trimethylsilyl triflate or a Lewis acid to form a β-anomeric nucleoside in high yield.

A convenient method for the synthesis of 2',3'-didehydro-2',3'-dideoxy nucleosides

9-(2,3-Dideoxy-β-D-glyceropent-2-enofuranosyl)adenine (2',3'-didehydro-2',3'-dideoxyadenosine, 9a), 9-(2,3-dideoxy-β-D-glyceropent-2-enofuranosyl)hypoxanthine (2',3'-didehydro-2',3'-dideoxyinosine, 9b) and 4-amino-7-(2,3-dideoxy-β-D-glyceropent-2-enofuran