433733-92-7

Usage

Uses

Used in Antiviral Applications:
2,2'-Anhydro-L-thymidine is used as an antiviral agent for its ability to inhibit the replication of viruses such as herpes simplex virus and human immunodeficiency virus.
Used in Cancer Therapy:
2,2'-Anhydro-L-thymidine is used as a potential candidate for cancer therapy due to its promising results in inhibiting the proliferation of tumor cells.
Used in Pharmaceutical Research:
2,2'-Anhydro-L-thymidine is used as a subject of ongoing research for its therapeutic applications, with potential implications for the treatment of viral infections and cancer.

Upstream product

• 35939-60-7 2-amino-β-L-arabinofurano[1',2':4,5]oxazoline 
• 51673-64-4 methyl 2-methyl-3-oxopropanoate 
• 433733-91-6 L-2,2'-anhydro-5,6-dihydrouridine-5-exomethylene 
• 27772-62-9 ethyl 2-formylpropionate 
• 129379-37-9 C₄H₄Cl₂O 
• 173009-66-0 1,2-di-O-acetyl-3,5-di-O-benzoyl-β-L-ribofuranose 
• 171721-12-3 1,2-di-O-isopropylidene-3,5-di-O-benzoyl-α-L-ribofuranose 
• 65-71-4 thymin 
• 849342-80-9 C₂₆H₂₄N₂O₉ 
• 26879-47-0 1-(β-L-ribofuranosyl)thymine 

Downstream Products

• 22423-25-2 2,2'-anhydro-1-(5-O-trityl-β-D-arabinofuranosyl)thymine 
• 817622-08-5 C₂₄H₂₀N₂O₇ 
• 849342-83-2 1-((2S,3S,4S,5S)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

PROCESS FOR PREPARING L-NUCLEIC ACID DERIVATIVES AND INTERMEDIATES THEREOF

A novel method has been found to produce 2,2′-anhydro-1-(β-L-arabinofuranosyl)thymine as a novel useful intermediate compound. A novel method has been further found to produce thymidine from 2,2′-anhydro-1-(β-L-arabinofuranosyl)thymine. According to these methods, synthesis of various L-nucleic acid derivatives, synthesis of which has been difficult till now, is possible.

Synthesis and anti-viral activity of a series of D- and l-2′-deoxy-2′-fluororibonucleosides in the subgenomic HCV replicon system

Based on the discovery of (2′R)-D-2′-deoxy-2′- fluorocytidine as a potent anti-hepatitis C virus (HCV) agent, a series of D- and L-2′-deoxy-2′-fluororibonucleosides with modifications at 5- and/or 4-positions were synthesized and evaluated for their in vitro activity against HCV and bovine viral diarrhea virus (BVDV). The key step in the synthesis, the introduction of 2′-fluoro group, was achieved by either fluorination of 2,2′-anhydronucleosides with hydrogen fluoride-pyridine or potassium fluoride, or a fluorination of arabinonucleosides with DAST. Among the 27 analogues synthesized, only the 5-fluoro compound, namely (2′R)-D-2′-deoxy-2′,5-difluorocytidine (13), demonstrated potent anti-HCV activity and toxicity to ribosomal RNA. The replacement of the 4-amino group with a thiol group resulted in the loss of activity, while the 4-methylthio substituted analogue (25) exhibited inhibition of ribosomal RNA. As N4-hydroxycytidine (NHC) had previously shown potent anti-HCV activity, we combined the two functionalities of the N4-hydroxyl and the 2′-fluoro into one molecule, resulting (2′R)-D-2′-deoxy- 2′-fluoro-N4-hydroxycytidine (23). However, this nucleoside showed neither anti-HCV activity nor toxicity. All the L-forms of the analogues were devoid of anti-HCV activity. None of the compounds showed anti-BVDV activity, suggesting that the BVDV system cannot always predict anti-HCV activity.

Synthesis of beta-L-2'-deoxy nucleosides

An improved process for the preparation of 2′-modified nucleosides and 2′-deoxy-nucleosides, such as, β-L-2′-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2′-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2′-anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2′-anhydro-1-furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2′-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2′-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.

L-NUCLEIC ACID DERIVATIVES AND PROCESSES FOR THE SYNTHESIS THEREOF

A novel method has been found to produce 2,2'-anhydro-1-(β-L-arabinofuranosyl)thymine as a novel useful intermediate compound. A novel method has been further found to produce thymidine from 2,2'-anhydro-1-(β-L-arabinofuranosyl)thymine. A novel method has been further found to L-2'-deoxyribose derivatives as a useful synthetic intermediate through L-2,2'-anhydro-5,6-dihydrocyclouridine derivative. According to these methods, synthesis of various L-nucleic acid derivatives, synthesis of which has been difficult till now.