433733-92-7

Basic information

• Product Name: 2,2'-Anhydro-L-thymidine
• Synonyms: 2,2'-Anhydro-L-thymidine;(2S,3S,3aR,9aS)-2,3,3a,9a-Tetrahydro-3-hydroxy-2-(hydroxymethyl)-7-methyl-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one;2,2'-Anhydro-1-(beta-L-arabinofuranosyl)thymine
• CAS NO: 433733-92-7
• Molecular Formula: C₁₀H₁₂N₂O₅
• Molecular Weight: 240.214
• Mol File: 433733-92-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 452.0±55.0 °C(Predicted)
• Appearance: /
• Density: 1.88±0.1 g/cm3(Predicted)
• Vapor Pressure: 0.001Pa at 20℃
• PKA: 12.56±0.60(Predicted)
• CAS DataBase Reference: 2,2'-Anhydro-L-thymidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Anhydro-L-thymidine(433733-92-7)
• EPA Substance Registry System: 2,2'-Anhydro-L-thymidine(433733-92-7)

Safety Data

• Hazardous Substances Data: 433733-92-7(Hazardous Substances Data)

Usage

Description

2,2'-Anhydro-L-thymidine (AHT) is a modified nucleoside that is structurally similar to thymidine, a component of DNA. AHT is created by removing the 2'-hydroxyl group from thymidine, resulting in a compound with potential antiviral and antitumor activities.

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

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

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 articles and documents

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 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.