6554-16-1

Usage

Uses

Used in Pharmaceutical Industry:
Cytidine, N-benzoyl-, 2',5'-dibenzoate is used as a potential therapeutic agent for its ability to modulate the activity of enzymes, which can be beneficial in the development of treatments for various diseases and conditions.
Used in Biochemistry Research:
Cytidine, N-benzoyl-, 2',5'-dibenzoate is used as a building block for the synthesis of nucleoside analogs and other biologically active molecules, contributing to the advancement of biochemical research and the discovery of new compounds with potential applications in medicine and other fields.

Upstream product

• 23624-64-8 N⁴-benzoyl-1-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)-cytosine 
• 80185-90-6 2',3'-O-(α-methoxybenzylidene)cytidine 
• 98-88-4 benzoyl chloride 

Relevant academic research and scientific papers

REGIOSELECTIVE PROTECTION OF CARBOHYDRATE DERIVATIVES. PART. 20. SIMPLE, EFFICIENT 2'-O-DEACYLATION OF FULLY ACYLATED PURINE AND PYRIMIDINE RIBONUCLEOSIDES THROUGH tert-BUTOXIDE

A simple treatment of fully aroylated purine and pyrimidine ribonucleosides with pulverized potassium tert-butoxide in tetrahydrofuran (THF) or dichloromethane under a controlled condition gave a mixture of the corresponding di-O-aroyl derivatives in which 2'-OH derivatives are preponderant over 3'-OH derivatives; 3',5'-di-O-benzoyluridine, N4,3',5'-tribenzoylcytidine, N4,3',5'-tri-O-toluoylcytidine, N2,3',5'-tribenzoylguanosine, and N2,isobutyryl-3',5'-di-O-benzoylguanosine were obtained crystalline in 80 percent, 78 percent, 72 percent, 67 percent, and 65 percent yields, respectively.

Synthesis of 2'(3')-O-Aminoacyl Triribonucleoside Diphosphates Using the Triester Method

Specific syntheses of 2'(3')-O-aminoacyl triribonucleoside diphosphates, C-C-A-Phe (16e), C-C-A-Ala (16f), and C-C-A-Gly (16g), which are the terminal sequences of corresponding aa-tRNAs and potential substrates for ribosomal peptidyltransferase, are described.The compounds 16e-g were synthesized by employing phosphotriester methods with a benzoyl group for protection of heterocyclic amino groups, a 2-chlorophenyl group for internucleotide phosphate protection, a monomethoxytrityl group for blocking of the 5'-hydroxy function, a 4-methoxytetrahydropyranyl group forprotection of 2'-hydroxy functions, and an N-benzyloxycarbonyl group for blocking of the α-amino acid.Protected dinucleotide block C-Cp (11b) was synthesized via the triester method and was condensed by using mesitylenesulfonyl tetrazolide with nucleoside components 9b and 10b, which have aminoacyl residues incorporated in the molecule, to yield protected aminoacyl trinucleotides 13a and 14 in 60-70percent yields.The fully protected aminoacyl trinucleotides 13a and 13b were also obtained from the protected C-C-A derivative 12 (with a free 3'-OH group on the 3'-terminus) by the aminoacylation reaction with corresponding N-benzyloxycarbonyl amino acids and mesitylenesulfonyl tetrazolide in 50-70percent yields.The protected derivatives 13a,b and 14 were deblocked to form C-C-A(Z-Phe) (16b), C-C-A(Z-Ala) (16c), and C-C-A(Z-Gly) (16d) in 15-40percent yields by reactions with N2H4, F-, and H+ (for 16b,c) or NH4OH and H+ (for 16d).The final products 16e-g were prepared by hydrogenolysis (Pd/BaSO4) of 16b-d in practically quantitative yields.The syntheses of all components (3a,c,4,9a,b, and 10b) for the triester approach to aminoacyl trinucleotides are also described.