130676-57-2

Basic information

• Product Name: 2',3'-Didehydro-2',3'-dideoxy-5'-acetate inosine
• Synonyms: 2',3'-Didehydro-2',3'-dideoxy-inosine 5'-acetate;2',3'-didehydro-2',3'-dideoxy-5'-acetate inosine;5-O-Acetyl-2`,3`-dideoxy-2`,3`-didehydroinosine;5-O-ACETYL-2'',3''-DIDEOXY-DIDEHYDROINOSINE
• CAS NO: 130676-57-2
• Molecular Formula: C12H12N4O4
• Molecular Weight: 276.251
• Mol File: 130676-57-2.mol

Chemical Properties

• Appearance: /
• Density: 1.60
• CAS DataBase Reference: 2',3'-Didehydro-2',3'-dideoxy-5'-acetate inosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-Didehydro-2',3'-dideoxy-5'-acetate inosine(130676-57-2)
• EPA Substance Registry System: 2',3'-Didehydro-2',3'-dideoxy-5'-acetate inosine(130676-57-2)

Safety Data

• Hazardous Substances Data: 130676-57-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2',3'-Didehydro-2',3'-dideoxy-5'-acetate inosine is used as an impurity in Inosine Pranobex, a formulation that is known to positively impact a host's immune system. Inosine Pranobex has been studied for its potential benefits in various conditions, including chronic fatigue syndrome and certain types of cancer, by modulating the immune response.
Used in Research and Development:
As a derivative of inosine, 2',3'-Didehydro-2',3'-dideoxy-5'-acetate inosine may be utilized in research and development for understanding the structure-activity relationships of nucleoside analogs. This could lead to the discovery of new therapeutic agents with improved pharmacological properties or novel applications in the treatment of various diseases.
Used in Quality Control and Analysis:
The presence of 2',3'-Didehydro-2',3'-dideoxy-5'-acetate inosine as an impurity in Inosine Pranobex necessitates its analysis and quantification in the quality control process. This ensures the safety, efficacy, and consistency of the pharmaceutical product, which is crucial for patient well-being and compliance with regulatory standards.

Upstream product

• 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 
• 58-63-9 Inosine 
• 108-24-7 acetic anhydride 

Downstream Products

• 42867-68-5 2',3'-didehydro-2',3'-dideoxyinosine 
• 130676-58-3 5'-O-acetyl-2',3'-dideoxyinosine 
• 389128-16-9 O⁶-benzyl-2',3'-dideoxyinosine 
• 389128-15-8 2',3'-dideoxy-O⁶-(2,4,6-triisopropylbenzenesulfonyl)inosine 
• 389128-13-6 5'-O-acetyl-2',3'-dideoxy-O⁶-(2,4,6-triisopropylbenzenesulfonyl)inosine 
• 389128-17-0 O⁶-benzyl-5'-O-dibenzyloxyphosphoryl-2',3'-dideoxyinosine 

Relevant articles and documents

Synthesis of 2',3'-dideoxy-2',3'-didehydro nucleosides via a serendipitous route.

This paper describes a "green" synthesis of 2',3'-unsaturated 2',3'-dideoxynucleosides via an electrochemical reaction. Using this approach d4T, d4U, ddA and ddI can be synthesized in high yields.

A process for the production of purine nucleoside compounds

The invention provides a process wherein a 3'-deoxy-3'-halopurine nucleoside compound is treated with perfluoroalkanesulfonyl fluoride in the presence of a base to give a 2',3'-didehydro-2',3'-dideoxypurine nucleoside compound. The resulting compound may be subjected to a catalytic hydrogenolysis to obtain a 2',3'-dideoxypurine nucleoside compound.

Synthesis of haptens for the development of immunoassays for the monitoring of intracellular anti-HIV nucleosides and nucleotides

A series of nine modified dideoxynucleosides and dideoxynucleotides has been synthesized for preparing antigenic conjugates with keyhole lympet haemocyanin in order to produce specific antibodies, and develop immunoassays. Derivatives of ddI, ddA, d4T, 3TC, and the corresponding 5′-O-monophosphates were designed incorporating an amino spacer at the base for conjugation with the proteinic antigenic carrier.

Process for preparing 2',3'-dideoxyadenosine

A process for preparing 2',3'-dideoxyadenosine of the formula STR1 wherein B is adenine, wherein R1 is hydrogen, C1-12 acyl, C1-12 alkyl, C7-8 aralkyl, or silyl, said process comprising: reducing a nucleoside of the formula IIIa or IIIb STR2 wherein R2 is hydrogen, C1-12 acyl, C1-12 alkyl, C7-8 aralkyl or silyl; X is Cl, Br or I; R5 is C1-12 acyl and B is adenine, with hydrogen in the presence of a palladium catalyst and aqueous solvent mixture of acetonitrile or ethyl acetate and water, said aqueous solvent containing a base selected from the group consisting of sodium hydroxide/sodium acetate and sodium carbonate/sodium acetate, wherein said solvent has a pH of 9-11.

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.