106060-78-0

Basic information

• Product Name: 5'-O-BENZOYL-3'-AZIDO-3'-DEOXYTHYMIDINE
• Synonyms: 5'-O-BENZOYL-3'-AZIDO-3'-DEOXYTHYMIDINE;ThyMidine, 3'-azido-3'-deoxy-, 5'-benzoate
• CAS NO: 106060-78-0
• Molecular Formula: C₁₇H₁₇N₅O₅
• Molecular Weight: 371.35
• Product Categories: Miscellaneous Biochemicals
• Mol File: 106060-78-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 5'-O-BENZOYL-3'-AZIDO-3'-DEOXYTHYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-BENZOYL-3'-AZIDO-3'-DEOXYTHYMIDINE(106060-78-0)
• EPA Substance Registry System: 5'-O-BENZOYL-3'-AZIDO-3'-DEOXYTHYMIDINE(106060-78-0)

Safety Data

• Hazardous Substances Data: 106060-78-0(Hazardous Substances Data)

Usage

General Description

5'-O-BENZOYL-3'-AZIDO-3'-DEOXYTHYMIDINE is a synthetic chemical compound that is used in biochemistry and molecular biology research. It is a modified form of thymidine, a nucleoside that is a building block of DNA. The compound is used in research to study DNA structure and function, as well as to develop new drugs and treatments for diseases. It contains a benzoate group and an azido group, which can be used to attach other molecules or labels for tracking and imaging purposes. The chemical has potential uses in gene therapy, drug delivery, and other biotechnological applications. Its unique structure and properties make it a valuable tool for studying and manipulating DNA in the laboratory.

Upstream product

• 30516-87-1 3'-azido-2',3'-deoxythymidine 
• 98-88-4 benzoyl chloride 
• 93-97-0 benzoic acid anhydride 
• 70838-44-7 2,3'-anhydro-5'-O-benzoyl-2'-deoxythymidine 
• 32649-51-7 dimethylammonium azide 
• 65-71-4 thymin 
• 362505-23-5 Methyl 5-O-benzoyl-3-azido-2,3-dideoxy-D-ribofuranoside 
• 65-85-0 benzoic acid 
• 120932-43-6 1-(5-O-benzoyl-2-deoxy-3-O-mesyl-β-D-xylofuranosyl)thymine 
• 165047-02-9 ((2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(methylsulfonyloxy)-tetrahydrofuran-2-yl)methyl benzoate 
• 50-89-5 thymidine 
• 165047-01-8 5′-benzoyl-3′α-methanesulfonyl-2′α-bromothymidine 
• 190003-82-8 1-(5-O-benzoyl-3-O-mesyl-β-D-xylofuranosyl)thymine 
• 220620-97-3 1-(5-O-benzoyl-2-chloro-2-deoxy-3-O-mesyl-β-D-xylofuranosyl)thymine 

Downstream Products

• 30516-87-1 3'-azido-2',3'-deoxythymidine 
• 1313201-66-9 C₂₁H₂₃N₅O₆ 
• 1313201-65-8 C₂₀H₂₁N₅O₆ 
• 1313201-84-1 C₂₂H₂₅N₉O₄ 
• 1313201-83-0 C₂₁H₂₃N₉O₄ 
• 1313201-82-9 C₂₀H₂₁N₉O₄ 
• 1313201-73-8 C₂₂H₂₄N₈O₅ 
• 1313201-72-7 C₂₁H₂₂N₈O₅ 
• 1313201-71-6 C₂₀H₂₀N₈O₅ 
• 1313201-67-0 C₂₂H₂₅N₅O₆ 
• 124355-23-3 1-(5-O-benzoyl-3-amino-2,3-dideoxy-β-D-erythro-pentofuranosyl)thymine 

Relevant articles and documents

A New Synthesis f the Anti-AIDS Drug AZT from 5-Methyluridine

The anti-AIDS drug AZT is prepared in six steps in 44percent overall yield starting from the readily available ribonucleoside 5-methyluridine.

Mechanisms of 5′-O-benzoyl-2,3′-anhydrothymidine reactions with nucleophiles: IV. Kinetics and thermodynamics of azidation with dimethylammonium azide in DMF-1,4-dioxane

The reaction of 5′-O-benzoyl-2,3′-anhydrothymidine with dimethylammonium azide in the system DMF-1,4-dioxane in the temperature range from 80 to 100°C follows the overall second-order kinetics and first-order kinetics with respect to each reactant. The activation parameters in the systems containing 30, 40, and 50 vol % of dioxane are, respectively: ΔH298≠ 99, 85, and 79 kJ/mol; ΔS 298≠ -46, -83, and -101 J mol-1 K -1. A refined model of the transition state for the rate-determining stage was proposed, which takes into account specific interaction with 1,4-dioxane.

Mechanisms of 5'-O-benzoyl-2,3'-anhydrothymidine reactions with nucleophiles: II. Kinetics of azidation with dimethylammonium azide in DMF-dioxane

The reaction of 5'-O-benzoyl-2,3'-anhydrothymidine with dimethylammonium azide in the system DMF-1,4-dioxane at 100°C follows the overall second-order kinetics or first-order in each of the reactants. Raising the dioxane fraction from 0 to 50 vol % accelerates the process due to low polarity of the transition state in the rate-determining stage.