20838-22-6

Usage

Uses

Used in Organic Synthesis:
3'-O,5'-O-Dibenzoyl-2'-deoxyadenosine is used as an intermediate in the synthesis of 1,3,5-Tri-O-benzoyl-2-deoxyribofuranose (T767660), a compound that is valuable in organic synthesis. This intermediate plays a crucial role in the development of new chemical compounds and materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3'-O,5'-O-Dibenzoyl-2'-deoxyadenosine is used as a building block for the development of new drugs. Its unique structure and properties make it a promising candidate for the creation of novel therapeutic agents.
Used in Research and Development:
3'-O,5'-O-Dibenzoyl-2'-deoxyadenosine is also utilized in research and development settings, where it can be employed to study the properties and interactions of various biological molecules. 3'-O,5'-O-Dibenzoyl-2'-deoxyadenosine can be used to investigate the mechanisms of action of different drugs and to develop a better understanding of their effects on biological systems.

Upstream product

• 78763-65-2 3',5'-Di-O-benzoyl-2'-O-thiobenzoyladenosine 
• 65-85-0 benzoic acid 
• 958-09-8 2'-deoxy-D-adenosine 
• 93-97-0 benzoic acid anhydride 
• 64723-02-0 N-benzoyl-3',5'-di-O-benzoyl-2'-deoxyadenosine 
• 51255-12-0 1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-D-erythro-pentafuranose 
• 17995-04-9 N,N-bis(trimethysilyl)adenine 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 303040-93-9 N⁶-benzoyl-3',5'-di-O-benzoyl-2'-O-[3-(trifluoromethyl)benzoyl]adenosine 
• 145828-13-3 α-D-1,3,5-tri-O-benzoyl-2-O-[3-(trifluoromethyl)benzoyl]ribofuranose 
• 613-90-1 benzoyl cyanide 
• 303040-96-2 3',5'-di-O-benzoyl-2'-O-[3-(trifluoromethyl)benzoyl]adenosine 
• 98-88-4 benzoyl chloride 

Downstream Products

• 958-09-8 2'-deoxy-D-adenosine 
• 3413-66-9 α-deoxyadenosine 
• 109584-91-0 5’-O-(4,4’-dimethoxytrityl)-2’-deoxy-1,N⁶-ethenoadenosine 
• 68498-25-9 3-(2-Deoxy-β-D-erythro-pentafuranosyl)-3H-imidazo[2,1-i]purine 

Relevant academic research and scientific papers

Mild, efficient, selective and "green" benzoylation of nucleosides using benzoyl cyanide in ionic liquid

Use of benzoyl cyanide (BzCN) for benzoylation of nucleosides has been studied, both in pyridine and in ionic liquid. BzCN in 1-methoxyethyl-3- methylimidazolium methanesulfonate as ionic liquid has been found to be a "green" alternative compared to the pyridine-BzCN system. An efficient and selective benzoylation of nucleosides of both, the 2′-deoxy- and the ribo-series at ambient temperature was accomplished. Copyright Taylor & Francis, Inc.

Benzoyl cyanide: A mild and efficient reagent for benzoylation of nucleosides

Efficient benzoylation of various nucleosides has been accomplished in pyridine with a catalytic amount of DMAP and benzoyl cyanide under mild conditions.

Enhanced solubility and selective benzoylation of nucleosides in novel ionic liquid

Solubility and benzoylation study of both ribo- and deoxyribonucleosides is reported in a new ionic liquid MoeMIM·TFA; high selectivity for O-benzoylation is achieved.

Continuous flow photochemistry for the rapid and selective synthesis of 2′-deoxy and 2′,3′-dideoxynucleosides

A new photochemical flow reactor has been developed for the photo-induced electron-transfer deoxygenation reaction to produce 2′-deoxy and 2′,3′-dideoxynucleosides. The continuous flow format significantly improved both the efficiency and selectivity of the reaction, with the streamlined multi-step sequence directly furnishing the highly desired unprotected deoxynucleosides.

Continuous flow photocatalysis enhanced using an aluminum mirror: Rapid and selective synthesis of 2′-deoxy and 2′,3′-dideoxynucleosides

A unique photochemical flow reactor featuring quartz tubing, an aluminum mirror and temperature control has been developed for the photo-induced electron-transfer deoxygenation reaction to produce 2′-deoxy and 2′,3′-dideoxynucleosides. The continuous flow format significantly increased the efficiency and selectivity of the reaction.

'Green' methodology for efficient and selective benzoylation of nucleosides using benzoyl cyanide in an ionic liquid

Benzoyl cyanide in the ionic liquid 1-methoxyethyl-3-methylimidazolium methanesulfonate has been employed as a 'green' alternative and mild reaction condition protocol to conventional pyridine-benzoyl chloride system for efficient and selective benzoylation of nucleosides (of both the ribo- and deoxyribo-series) at ambient temperatures. The use of benzoyl cyanide-ionic liquid combination has been successfully extended for highly efficient benzoylation of phenols, aromatic amines, benzyl alcohol, aliphatic diols, 3-aminophenol and 2-aminobenzylalcohol, which indicates the versatility of this benzoylating system.

Stereocontrolled Syntheses of Deoxyribonucleosides via Photoinduced Electron-Transfer Deoxygenation of Benzoyl-Protected Ribo- and Arabinonucleosides

The stereocontrolled, de novo syntheses of β-2′-deoxy-, α-2′-deoxy-, β-3′-deoxy-, and β-2′,3′-dideoxyribonucleosides are described. Strategically protected ribose, arabinose, and xylose glycosylation precursors were synthesized bearing C2-esters capable of directing Vorbrueggen glycosylation. The key step is the regioselective deoxygenation of the desired hydroxyl group as either the benzoyl- or 3-(trifluoromethyl)benzoyl derivative. This deoxygenation is accomplished via a photoinduced electron-transfer (PET) mechanism using carbazole derivatives as the photosensitizer. The syntheses of the desired deoxynucleoside generally proceed in three steps from a common, readily available precursor.

Stabilization of deoxyadenosine/polynucleotide complexes by 3',5'-Di-O- benzoyl substituents

3',5'-Di-O-benzoyldeoxyadenosine forms stable dT:dA:dT type complexes with poly(dT) and an oligo(dT)-cholesteryl conjugate in dilute aqueous solution. The benzoyl groups play an essential role in stabilizing these 'triple stranded' complexes.