62374-25-8

Usage

Uses

Used in Research Applications:
2'',3'',5''-Tri-O-benzoylguanosine is used as a starting material for the synthesis of modified nucleosides and nucleotides with potential biological activities. Its hydrophobic and less polar nature allows for the development of compounds that can interact differently with biological systems, making it a valuable tool in the study of RNA and protein synthesis.
Used in Pharmaceutical Applications:
2'',3'',5''-Tri-O-benzoylguanosine is used as a precursor in the development of new drugs and therapeutic agents. Its unique chemical properties enable the creation of modified nucleosides and nucleotides that can potentially target specific biological pathways or interact with enzymes, offering new avenues for the treatment of various diseases and conditions.

Upstream product

• 28288-50-8 N²,2',3',5'-tetrabenzoylguanosine 
• 28288-50-8 N²,O^2',O^3',O^5'-tetrabenzoylguanosine 

Downstream Products

• 78763-66-3 2'-O-(Thiobenzoyl)-N²,3'-O,5'-O-tribenzoylguanosine 

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.

Partial Protection of Carbohydrate Derivatives. Part 4. Regioselective 2'-O-Deacylation of Fully Acylated Purine and Pyrimidine Ribonucleosides with Hydroxylaminium Acetate

Like hydrazine hydrate, hydroxylamine was found to be useful for the regioselective 2'-O-deacylation of fully acylated purine and pyrimidine ribonucleosides as its salt with acetic acid; the partial O-deacylation reactions (which were not accompanied by undesirable discolouration as happens with hydrazine hydrate) gave the corresponding di-O-acylribonucleosides in superior yields; e.g. 2',3'-di-O-benzoyladenosine (74percent yield), 3',5'- (64percent yield) and 2',5'-di-O-benzoyl-N6-benzyladenosine (63percent yield on performing the reaction in ethanol), N2,3',5'-tri-O-benzoylguanosine (66percent yield), N2,2',5'-tri-isobutyrylguanosine (48percent yield), and 3',5'-di-O-benzoyluridine (61percent yield) were obtained using hydroxylaminium acetate in pyridine.Treatment of fully acetylated ribonucleosides with an excess of hydroxylaminium acetate gave the corresponding 5'-O-acetylribonucleosides in quantitative yields.The excellent regioselectivity observed in the present partial O-decyclation was confirmed on the basis of chromatographic separation; the mixtures of di-O-acylribonucleosides, which had already been equilibrated in pyridine, were re-equilibrated on the silica gel during separation, e.g. a 70 : 30 mixture of 3',5'- and 2',5'-di-O-benzoyladenosine was completely converted into the former based on 1H n.m.r spectroscopy.The acetates of 9-β-D-xylo- and -arabino-furanosyladenine were also found to give predominantly the corresponding 3',5'-diacetates on hydroxylaminolysis.