5964-41-0

Basic information

• Product Name: 5'-O-TRITYL-2',3'-DEHYDROTHYMIDINE
• Synonyms: 5'-O-TRITYL-2',3'-DEHYDROTHYMIDINE;5-methyl-1-(5-trityloxymethyl-2,5-dihydro-furan-2-yl)-1H-pyrimidine-2,4-dione;2',3'-Dehydro-5'-O-trityl-D-thymidine;2,3-DIDEHYDRO-3-DEOXY-5-O-(TRIPHENYLMETHYL)-THYMIDINE(KEY INTERMEDIATE OF ZIDOVUDINE:AZT);2',3'-Dehydro-5'-O-tritylthymidine
• CAS NO: 5964-41-0
• Molecular Formula: C₂₉H₂₆N₂O₄
• Molecular Weight: 466.52774
• Product Categories: Bases & Related Reagents;Nucleotides
• Mol File: 5964-41-0.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Density: 1.24g/cm³
• Refractive Index: 1.616
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: 5'-O-TRITYL-2',3'-DEHYDROTHYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-TRITYL-2',3'-DEHYDROTHYMIDINE(5964-41-0)
• EPA Substance Registry System: 5'-O-TRITYL-2',3'-DEHYDROTHYMIDINE(5964-41-0)

Safety Data

• Hazardous Substances Data: 5964-41-0(Hazardous Substances Data)

Usage

Description

5'-O-TRITYL-2',3'-DEHYDROTHYMIDINE, with the CAS number 5964-41-0, is a white solid compound that is primarily utilized in the field of organic synthesis. It is a derivative of thymidine, a nucleoside that plays a crucial role in DNA and RNA synthesis. The trityl group attached to the 5' position and the absence of the 2' and 3' hydroxyl groups in the sugar moiety make this compound unique and valuable for various applications in chemical research and synthesis.

Uses

Used in Organic Synthesis:
5'-O-TRITYL-2',3'-DEHYDROTHYMIDINE is used as an intermediate in organic synthesis for the development of novel compounds with potential applications in various industries. Its unique structure allows for selective reactions and modifications, making it a versatile building block for the creation of new molecules with specific properties and functions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5'-O-TRITYL-2',3'-DEHYDROTHYMIDINE is used as a key compound in the synthesis of antiviral and anticancer drugs. Its ability to be selectively modified and its interaction with biological targets make it a promising candidate for the development of new therapeutic agents.
Used in Research and Development:
5'-O-TRITYL-2',3'-DEHYDROTHYMIDINE is also used in research and development laboratories for studying the mechanisms of nucleic acid synthesis, replication, and repair. Its unique properties allow researchers to investigate the role of thymidine and its derivatives in various biological processes, leading to a better understanding of DNA and RNA functions and the development of targeted therapies.
Used in Chemical Education:
As an educational tool, 5'-O-TRITYL-2',3'-DEHYDROTHYMIDINE can be employed in teaching organic chemistry and biochemistry courses to demonstrate the synthesis and manipulation of complex organic molecules. Its unique structure and reactivity provide students with valuable insights into the principles of organic synthesis and the importance of nucleosides in biological systems.

InChI:InChI=1/C29H26N2O4/c1-21-19-31(28(33)30-27(21)32)26-18-17-25(35-26)20-34-29(22-11-5-2-6-12-22,23-13-7-3-8-14-23)24-15-9-4-10-16-24/h2-19,25-26H,20H2,1H3,(H,30,32,33)/t25-,26+/m0/s1

Upstream product

• 64-17-5 ethanol 
• 42214-24-4 1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine 
• 25442-42-6 5'-O-trityl-2,3'-anhydrothymidine 
• 7791-71-1 5'-O-tritylthymidine 
• 1463-10-1 5-Methyluridine 
• 101796-28-5 1-(5'-O-trityl-β-D-ribofuranosyl)thymine 
• 444786-36-1 1-{1-[1-(trityloxymethyl)prop-2-enyloxy]prop-2-enyl}thymine 
• 1190-73-4 2-(acetylamino)ethanethiol 
• 5862-40-8 2-mercaptoethyl acetate 
• 3483-12-3 diothiothreitol 
• 96-27-5 rac-3-sulfanylpropane-1,2-diol 
• 104218-44-2 1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-threo-pentofuranosyl)thymine 
• 100-46-9 benzylamine 
• 74-89-5 methylamine 

Downstream Products

• 142545-13-9 1-(2,3-anhydro-5-O-trityl-β-D-lyxofuranosyl)-2-O-methylthymine 
• 115913-84-3 1-(2,3-epoxy-5-O-trityl-β-D-lyxo-pentofuranosyl)thymine 
• 3929-76-8 furfuryl triphenylmethylether 
• 3056-17-5 stavudin 
• 145819-51-8 2,2'-anhydro-1-(3'-deoxy-3'-bromo-5'-O-trityl-β-D-arabinofuranosyl)-(5R,6R)-trans-5-bromo-6-hydroxy-5,6-dihydrothymine 
• 145919-54-6 2,2'-anhydro-1-(3'-deoxy-3'-bromo-5'-O-trityl-β-D-arabinofuranosyl)-(5S,6S)-trans-5-bromo-6-hydroxy-5,6-dihydrothymine 
• 145819-53-0 2,2'-anhydro-1-(3'-deoxy-3'-bromo-5'-O-trityl-β-D-arabinofuranosyl)thymine 
• 159353-49-8 (5R,6R)-2,2'-anhydro-5-bromo-1-(3'-bromo-3'-deoxy-5'-O-trityl-β-D-arabinofuranosyl)-6-methoxy-5,6-dihydrothymine 
• 159407-15-5 (5S,6S)-2,2'-anhydro-5-bromo-1-(3'-bromo-3'-deoxy-5'-O-trityl-β-D-arabinofuranosyl)-6-methoxy-5,6-dihydrothymine 

Relevant articles and documents

New 3′-deoxythymidines bearing a nucleophilic 3′-substituent

New potential cancer-driven as well as HIV-driven nucleoside heteroanalogs, such as 3′-thio- and 3′- as well as 5′-selenosubstituted thymidines, have been synthesized. We also report an effective method for the preparation of novel nucleoside derivatives, bis(deoxynucleoside) diselenides, in nearly quantitative yields. The North conformation is significantly populated in the conformational equilibrium for 3′-α-alkylthiothymidines.

A novel approach to unsaturated acyclic nucleoside analogues and the first synthesis of d4T by ring closure metathesis

Novel unsaturated acyclic nucleoside analogues, 1-{1-[1-(hydroxymethyl)prop-2-enyloxy]prop-2-enyl}uracil, 1-{1-[1-(hydroxymethyl)prop-2-enyloxy]prop-2-enyl}thymine and 1-{1-[1-(hydroxymethyl)prop-2-enyloxy]prop-2-enyl}cytosine have been prepared in good yield from uridine and 5-methyluridine by periodate cleavage followed by a double Wittig reaction which introduces two vinyl groups. The thymine derivative underwent ring closure metathesis to give a novel synthesis of d4T.

Synthesis of 2′,3′-Didehydro-2′,3′-dideoxynucleosides by Reaction of 5′-O-Protected Nucleoside 2′,3′-Dimesylates with Lithium Areneselenolates

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