4449-39-2

Basic information

• Product Name: 3',5'-DI-O-(4-METHYLBENZOYL)-THYMIDINE
• Synonyms: 3',5'-DI-O-(4-METHYLBENZOYL)-THYMIDINE
• CAS NO: 4449-39-2
• Molecular Formula: C₂₆H₂₆N₂O₇
• Molecular Weight: 478.49384
• Mol File: 4449-39-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 197 °C
• Appearance: /
• Density: 1.35±0.1 g/cm3(Predicted)
• PKA: 9.55±0.10(Predicted)
• CAS DataBase Reference: 3',5'-DI-O-(4-METHYLBENZOYL)-THYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3',5'-DI-O-(4-METHYLBENZOYL)-THYMIDINE(4449-39-2)
• EPA Substance Registry System: 3',5'-DI-O-(4-METHYLBENZOYL)-THYMIDINE(4449-39-2)

Safety Data

• Hazardous Substances Data: 4449-39-2(Hazardous Substances Data)

Upstream product

• 874-60-2 4-methyl-benzoyl chloride 
• 50-89-5 thymidine 
• 3056-13-1 3',5'-di-O-p-toluoyl-2'-deoxythymidine 
• 4330-34-1 methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose 
• 10416-59-8 N,O-Bis(trimethylsilyl)acetamide 
• 65-71-4 thymin 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 

Downstream Products

• 3056-13-1 3',5'-di-O-p-toluoyl-α-2'-deoxythymidine 
• 4449-43-8 α-deoxythymidine 
• 4784-41-2 1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl)thymine 
• 1335213-63-2 C₅₄H₆₄N₄O₁₁S₂ 
• 1335213-64-3 C₃₈H₅₂N₄O₉S₂ 
• 50-89-5 thymidine 

Relevant articles and documents

FACILE STEREOSPECIFIC SYNTHESIS OF α-ANOMERIC 2'-DEOXYNUCLEOSIDES

The coupling reaction of activated nucleobases, such as the sodium salts of N-benzoyladenine and 6-chloropurine and 2,4-bis-O-trimethylsilylthymine, with 1-α-chloro-2-deoxy-3,5-di-O-p-toluoylribofuranose (1) in a mixture of acetonitrile and tetrahydrofuran leads to the stereospecific formation of α-anomeric 2'-deoxynucleosides with satisfactory yields.The ratio of the distribution between the resulted α- and β-stereoisomers was about 3:1 in each case.The method is simple and applicable to the preparation of both purine and pyrimidine α-2'-deoxynucleosides.

Substituent and solvent effects of TMS triflate mediated C1′ epimerization of β-thymidine to α-thymidine

This paper deals with kinetic studies of TMSOTf-mediated C1′ epimerization of β-thymidine to α-thymidine. The effect of neighboring group participation by various 5′-hydroxy protecting groups, such as toluoyl, Et2CHC(O), Et2NC(O), and Et2NC(S), on the β→α conversion is described in detail. The time dependence of the ratio of the α and β anomers in the C1′ epimerization was estimated by 1H NMR. The α/β equilibrium constants K and the rate constants kα and kβ were calculated on the basis of the experimental data. As the result, it was concluded that, in acetonitrile, the α/β equilibrium constants K are thermodynamically affected by steric hindrance from the 5′-hydroxy protecting group. On the other hand, the rate constants kα and kβ are mainly influenced by the stability of the oxonium ion intermediate. In particular, formation of an intramolecularly cyclized iminium ion intermediate from the oxonium ion intermediate, due to the neighboring group participation by the diethylthiocarbamoyl group, tended to decrease the overall reaction rate. Finally, the α/β C1′ epimerization could be carried out with a high α anomer selectivity of 89% through the use of the Et2CHC(O) group. Thus, 5′-O-pixyl-α-thymidine could be synthesized from β-thymidine as a key intermediate for the synthesis of α-DNA in a considerably improved overall yield of 40%.

Synthesis of α-2'-deoxynucleosides

α-Thyimdine (4) was synthesized from thyimdine (1) in 3 steps in 36% overall yield without using chromatography and with the possibility of increasing the yield to 85% by reusing the remaining α,β-mixture. 1-(2-Deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofu