73971-82-1

Basic information

• Product Name: 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione
• Synonyms: 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione;1-(3-beta-Azido-2,3-dideoxy-beta-D-threopenta-furanosyl)thyMine;3'-epi-Azido-3'-deoxythyMidine;3'-beta-Azido-3'-deoxy thyMidine;AZT(threo), AzddXyloT;1-(3-Azido-2,3-dideoxy-beta-D-threo-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione
• CAS NO: 73971-82-1
• Molecular Formula: C₁₀H₁₃N₅O₄
• Molecular Weight: 0
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals, Nucleotides, Bases & Related Reagents
• Mol File: 73971-82-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione(73971-82-1)
• EPA Substance Registry System: 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione(73971-82-1)

Safety Data

• Hazardous Substances Data: 73971-82-1(Hazardous Substances Data)

Usage

Description

1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione is a complex organic compound with a unique molecular structure. It is characterized by its azido, hydroxymethyl, and oxolan-2-yl groups, which contribute to its potential applications in various fields. 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione is a derivative of pyrimidine-2,4-dione, which is a common structural motif in many biologically active molecules.

Uses

Used in Pharmaceutical Industry:
1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione is used as a pharmaceutical compound for its potential therapeutic applications. The presence of the azido group and the hydroxymethyl group in its structure may allow for the development of new drugs with unique mechanisms of action, targeting specific diseases or conditions.
Used in Antiviral Applications:
As an analog of 3'-Azido-3'-deoxythymidine (AZT), 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione may be used as an antiviral agent, particularly against HIV-1. The azido group in its structure could potentially inhibit viral replication by integrating into the viral DNA, thus preventing further replication of the virus.
Used in Drug Delivery Systems:
Similar to gallotannin, 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione could be employed in the development of novel drug delivery systems. Its unique structural features may allow for the design of targeted drug carriers, improving the bioavailability and therapeutic outcomes of various drugs.
Used in Chemical Synthesis:
1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione may also find use in chemical synthesis, as a building block for the creation of more complex molecules with specific biological activities. Its azido and hydroxymethyl groups could be utilized in various chemical reactions, leading to the formation of new compounds with potential applications in medicine, agriculture, or other industries.

Upstream product

• 7791-71-1 5'-O-tritylthymidine 
• 135281-03-7 5-O-acetyl-3-azido-1-O-(4-biphenylcarbonyl)-2,3-dideoxy-D-threo-pentofuranose 
• 122359-33-5 (+)-(2E,4S)-5-Acetoxy-4-(formyloxy)-2-pentenal 
• 135357-51-6 (2E,4S)-5-acetoxy-4-hydroxy-2-pentenal 
• 371164-34-0 4,5-O-cyclohexylidene-2,3-dideoxy-3-azido-aldehydo-D-glycero-pentanose 
• 114647-74-4 4,5-O-cyclohexylidene-2,3-dideoxy-aldehydo-D-glycero-trans-pent-2-enose 
• 42214-24-4 1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 371164-35-1 4,5-O-cyclohexylidene-2,3-dideoxy-3-azido-1,1-dimethoxy-D-glycero-pentanose 
• 66503-47-7 1-(3-Azido-2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine 

Relevant articles and documents

Synthesis and anti-HIV activity of triazolo-fused 3′,5′-cyclic nucleoside analogues derived from an intramolecular Huisgen 1,3-dipolar cycloaddition

Triazolo-fused 3′,5′-cyclic nucleoside analogues were synthesized by an intramolecular 1,3-dipolar cycloaddition of nucleoside-derived azido-alkynes in a regio- and stereospecific manner. The thymine nucleoside base in these target compounds was transform

A novel synthesis of AZT

A novel synthesis of AZT has been achieved from two commercial available products acetaldehyde and D-mannitol. The originality of the synthesis consists of using the powerful monovinylogation reagent, the 2-lithio-1-trimethylsiloxyethylene, and to introduce the thymine moiety and to build the furanose ring in the same and last step.

3'-Substituted 2',3'-Dideoxynucleoside Analogues as Potential Anti-HIV (HTLV-III/LAV) Agents

A series of 2',3'-unsaturated and 3'-substituted 2',3'-dideoxynucleoside analogues of purines and pyrimidines have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV).The 2',3'-unsaturated analogues of 2',3'-dideoxycytidine (ddeCyd) and 2',3'-dideoxythymidine (ddeThd), 3'-azido-2',3'-dideoxythymidine (AzddThd), 3'-fluoro-2',3'-dideoxythymidine, 2',3'-dideoxycytidine (ddCyd), and 2',3'-dideoxyadenosine (ddAdo) emerged as the most potent inhibitors of HIV-induced cytopathogenicity in the human T lymphocyte cell lines ATH8 and MT4.In ATH8 cells ddCyd, ddeCyd, and ddAdo had the highest therapeutic index whereas in MT4 cells AzddThd, ddThd, ddCyd, and ddAdo were the most selective.Derivatives from ddThd in which the substituent group was linked to the 3'-carbon atom via a thio, sulfonyl, or oxygen bridge were far less inhibitory to HIV than was AzddThd.