4449-38-1

Upstream product

• 106-43-4 para-chlorotoluene 
• 951-78-0 2'-deoxyuridine 
• 3992-42-5 2'-deoxycytidine monohydrochloride 
• 874-60-2 4-methyl-benzoyl chloride 
• 4330-34-1 methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose 
• 10416-59-8 N,O-Bis(trimethylsilyl)acetamide 
• 66-22-8 uracil 

Downstream Products

• 31356-86-2 1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-iodouracil 
• 81777-57-3 5-chloro-3',5'-di-O-p-toluyl-2'-deoxyuridine 
• 944148-98-5 2'-deoxy-3',5'-bis-O-(4-toluoyl)-4-O-[(2,4,6-triisopropylbenzene)sulfonyl]uridine 

Relevant academic research and scientific papers

Synthesis of carbohydrate-conjugated dT analogues using 'click chemistry'

A new type furo[2,3-d]pyrimidine nucleoside conjugated with various carbohydrates was synthesized using Sonogashira coupling and 'click chemistry'. In the subsequent deprotection of the 4-toluoyl and acetyl groups with catalytic sodium methoxide in methan

Hydrothermal deamidation of 4-N-acylcytosine nucleoside derivatives: Efficient synthesis of uracil nucleoside esters

(Chemical Equation Presented) N,O-Peracylated cytidine and 2′-deoxycytidine derivatives in superheated water/DME solutions (oil bath at 125°C) undergo hydrolytic deamidation (and/or N-deacylation). Acylated starting materials derived from arylcarboxylic acids give the corresponding uridine esters cleanly, and such derivatives crystallize selectively from the cooled reaction mixtures in high yields.

Investigation of Stereoselectivities in the Coupling Reactions of 1-O-Methyl-3,5-di-O-p-toluoyl-2-deoxyribofuranoside with Purines and Pyrimidines

Stereoselectivities in the coupling rection between 1-O-methyl-3,5-di-O-p-toluoyl-2-deoxyribofuranoside and suitably protected purine and pyrimidine derivatives have been examined in acetonitrile with varying equivalents of SnCl4.The best result in α-nucleoside formation was obtained when the coupling reaction was carried out in the presence of ten equivalents of SnCl4.

Nucleic acid related compounds. 38. Smooth and high-yield iodination and chlorination at C-5 of uracil bases and p-toluyl-protected nucleosides

Treatment of uracil bases and protected nucleosides with iodine monochloride (ICl) gave the corresponding 5-iodouracil products in over 95percent purified yields.Analogously facile chlorination was effected with iodobenzene dichloride (PhICl2).Protection of the nucleosides as p-toluyl esters provided reactants that were soluble in organic solvents and crystallized readily in high yields.